Indolizidine 167B与Cremastrine的全合成研究
摘要
本论文对吲哚里西定(Indolizidine)类生物碱Indolizidine 167B及双稠吡咯烷(pyrrolizidine)类生物碱Cremastrine进行了全合成研究。共包括以下三个部分:
一、Weinreb amides在有机合成中的应用(综述)
本部分介绍了Weinreb amides的发现、反应机理与制备方法,以及Weinrebamides的相关反应在在官能团转化、碳链延长、结构拼接中的应用。
二.Indolizidine 167B的合成研究
本部分介绍了吲哚里西定(Indolizidine)类生物碱的定义、简况以及合成研究。并以Boc-L-脯氨酸为原料,经Weinreb酰胺化反应,乙炔格氏试剂的取代反应,分子内氮参与的1,4加成反应,及分子间迈克尔加成反应,合成了Indolizidine 167B前体化合物。
三、Cremastrine的合成研究
本部分介绍了双稠吡咯烷(pyrrolizidine)类生物碱的定义、简况以及合成研究。设计了以脯氨酸与苏氨酸为起始原料,以迪克曼缩合与环氧化反应为关键步骤,对双稠吡咯烷(pyrrolizidine)类生物碱Cremastrine进行全合成研究。
This thesis main focused on the syntheses of Indolizidine 167B and Cremastrine.Its included the following three parts:
Chapter 1.Chemistry of Weinreb amides,and applications in organic synthesis.(review).
The preparation of Weinreb amides was introduced in detail.The important applications in organic synthesis were also reviewed.
Chapter 2.Synthesis of Indolizidine 167B.
The definition,previous synthetic reports of Indolizidine alkaloid were introduced in brief.The precursor of Indolizidine 167B was obtained from Boc-L-proline as starting material via substitution reaction,intramolecular aza-micheal addition reaction and intermolecular micheal addition reaction
Chapter 3.Synthesis of Cremastrine.
The definition,previous synthetic reports of Pyrrolizidine alkaloid were introduced in brief.The approach of synthesis of Cremastrine was studied starting from L-Proline and L-threonine.In which Dieckmann reaction and epoxidation were key steps.
一、Weinreb amides在有机合成中的应用(综述)
本部分介绍了Weinreb amides的发现、反应机理与制备方法,以及Weinrebamides的相关反应在在官能团转化、碳链延长、结构拼接中的应用。
二.Indolizidine 167B的合成研究
本部分介绍了吲哚里西定(Indolizidine)类生物碱的定义、简况以及合成研究。并以Boc-L-脯氨酸为原料,经Weinreb酰胺化反应,乙炔格氏试剂的取代反应,分子内氮参与的1,4加成反应,及分子间迈克尔加成反应,合成了Indolizidine 167B前体化合物。
三、Cremastrine的合成研究
本部分介绍了双稠吡咯烷(pyrrolizidine)类生物碱的定义、简况以及合成研究。设计了以脯氨酸与苏氨酸为起始原料,以迪克曼缩合与环氧化反应为关键步骤,对双稠吡咯烷(pyrrolizidine)类生物碱Cremastrine进行全合成研究。
This thesis main focused on the syntheses of Indolizidine 167B and Cremastrine.Its included the following three parts:
Chapter 1.Chemistry of Weinreb amides,and applications in organic synthesis.(review).
The preparation of Weinreb amides was introduced in detail.The important applications in organic synthesis were also reviewed.
Chapter 2.Synthesis of Indolizidine 167B.
The definition,previous synthetic reports of Indolizidine alkaloid were introduced in brief.The precursor of Indolizidine 167B was obtained from Boc-L-proline as starting material via substitution reaction,intramolecular aza-micheal addition reaction and intermolecular micheal addition reaction
Chapter 3.Synthesis of Cremastrine.
The definition,previous synthetic reports of Pyrrolizidine alkaloid were introduced in brief.The approach of synthesis of Cremastrine was studied starting from L-Proline and L-threonine.In which Dieckmann reaction and epoxidation were key steps.
引文
1.S.Nahm and S.M.Weinreb,N-methoxy-N-methylamides as effective acylating agents.Tetrahedron Lett,1981,22,3815.
2.O.P.Goel and U.Krolls,Org.Prep.Proced.Int,1987,19,75 and references cited therein
3.J.A.Fehrentz and B.Castro,Synthesis,1983,676.
4.I.Maugras,J.Poncet and P.Jouin,A synthetic approach to the plakoridines modeled on a biogenetic theory,Tetrahedron,1990,46,2807.
5.M.Braun and D.Waldmuller,Synthesis,1989,856.
6.D.T.Davies and P.J.Hanlon,Synth.Commun,1988,18,2273.
7.W.Oppolzer and A.F.Cunningham,Total synthesis of(±)chokol-A via an intramolecular type-Ⅰ-magnesium ene reaction.Tetrahedron Lett,1986 27,5467.
8.N.Irako,Y.Hamada and T.Shioiri,A new efficient synthesis of(S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine),the C-terminal unit of dolastatin.Tetrahedron,1992,48,7251.
9.Castro,B.;Dormoy,J.R.;Evin,G.;Selve,C.Zur cycloaddition von arylisocyanaten an ε-caprolactimather.Tetrahedron Lett.1975,14,1219.
10.Dormoy,J.R.;Castro,B.,The reaction of hexamethyl phosphoric triamide (HMPT)with phosphoryl chloride:A reexamination.Application to a novel preparation of BOP reagent for peptide coupling.Tetrahedron Lett.1979,20,3321.
11. Le-Nguyen, D.; Heitz, A.; Castro, B. J. Chem. Soc. Perkin Trans.I 1987,1915
12. Coste, J.; Le-Nguyen, D.; Castro, B. PyBOP~(?): A new peptide coupling reagent devoid of toxic by-product. Tetrahedron Lett. 1990,31,205.
13. Kahl, J. D. ; Greenberg, M. M. Introducing Structural Diversity in Oligonucleotides via Photolabile, Convertible C5-Substituted Nucleotides J.Am. Chem. Soc. 1999,121, 597.
14. Crowley, B. M. ; Mori, Y. ; McComas, C. C. ; Tang, D. ; Boger, D. L. Total Synthesis of the Ristocetin Aglycon. J.Am. Chem. Soc. 2004,126,4310.
15. You, S. -L. ; Kelly, J. W. The total synthesis of bistratamides F-I. Tetrahedron, 2005,61,241.
16. Lee, J.; Griin, J. H.; Nicas, T. I. Solid-Phase. Total Synthesis of Bacitracin A . J. Org. Chem. 1996, 61, 3983.
17. J. Einhorn, ; C. Einhorn and J. -L. Luche. A convenient method for the preparation of N-methoxyamides, Synth. Commun. 1990,20, 1105.
18. P. Kocienshi, M. Stocks,; D. Donald and M. Perry, Synlett, 1990 38
19. R. S. Garigipati, ; D. M. Tschaen and S. M. Weinreb, Total synthesis of (+)-actinobolin. J. Am. Chem. Soc, 1985,107, 7790.
20. D. A. Evans, ; S. J. Miller. ; M, D, Ennis and P. L. Ornstein, Asymmetric synthesis of macbecin I. J. Org. Chem. 1992, 57,1067
21. J. Michael. Williams. ;Ronald. B. Jobson.; Nobuyoshi. Yasuda.; George. Marc- hesini.; Ulf-H. Dolling and Edward. J. J. Grabowsk. A New General Method for Preparation of N.Methoxy-N-Methylamides. Application in Direct Conversion of an Ester to a Ketone. Tetrahedron Lett. 1995, 36, 5461.
22. Ashok. Rao. Tunoori. ; Jonathan. M. White and Gunda. I. Georg. A one-flask synthesis of Weinreb amides rom chiral and achiral carboxylic acids using the Deoxo-fluor luorinating reagent Organic Letters 2000,2,4091.
23. Miguel. A. Baile'n.; Rafael. Chinchilla.; David. J. Dodsworth and Carmen. Na'jera. Direct synthesis of hydroxamates from carboxylic acids using 2-mercaptopyridone-1-oxide-based thiouronium salts. Tetrahedron Lett. 2001, 42, 5013.
24 Jacqueline.C.S.Woo.;Erik.Fenster.;and Gregory.R.Dake.A Convenient Method for the Conversion of Hindered Carboxylic Acids to N-Methoxy-N-methyl (Weinreb)Amides.J.Org.Chem.2004,69,8984.
25.Carolyn.A.Leverett.;Michael.P.Cassidy and Albert.Padwa.Application of the Aza-Achmatowicz Oxidative Rearrangement for the Stereoselective Synthesis of the Cassia and Prosopis Alkaloid Family.J.Org.Chem.2006,71.8591.
26.Kavirayani.R.Prasad.and Pazhamalai.Anbarasan.An enantiospecific synthesis of(+)-hydroxy-exo-brevicomin.Tetrahedron Lett.2006,47,1433.
27.Kavirayani.R.Prasad.and Pazhamalai.Anbarasan.Stereoselective synthesis of (+)-boronolide and(-)-5-epi-boronolide.Tetrahedron Asymmetry 2006,17,1146.
28.Seung-Mann.Paek.;Seung-Yong,Seo.;Seok-Ho.Kim.;Jong-Wha.Jung.;Yong-Sil.Lee.;Jae-Kyung.Jung.and Young-Ger.Sub.Concise Syntheses of (+)-Macrosphelides A and B.Organic Letters.2005,7,3159.
29.Organic Syntheses.1993,8,68.
30.John.A.Murphy.;Aurelien.G.J.Commeureuc.;Thomas.N.Snaddon.;Thomas.M.McGuire.;Tanweer.A.Khan.;Kevin.Hisler.;Mark.L.Dewis.and Robert.Carling.Direct Conversion of N-Methoxy-N-methylamides (Weinreb Amides)to Ketones via a Nonclassical Wittig Reaction.Organic Letters.2005,7,1427.
31.Javier.Ruiz.;Nuria.Sotomayor.and Esther.Lete.Parham-Type Cycliacylation with Weinreb Amides.Application to the Synthesis of Fused Indolizinone Systems.Organic Letters.2003,5,1115.
32.Angel.Alberola.;Alfonso.Gonalez.Ortega.;M.Luisa.Sadaba.and Carmen.Sanudo.Versatility of Weinreb amides in the Knorr Pyrrole Synthesis.Tetrahedron.1999,55,6555.
33.Takashi.Ooi.;Mifune.Takeuchi.;Daisuke.Kato.;Yuldtaka.Uematsu.;Eiji.Tayama.;Daiki.Sakai.and Keiji.Maruoka.Highly Enantioselective Phase-Transfer-Catalyzed Alkylationof Protected r-Amino Acid Amides toward PracticalAsymmetric Synthesis of Vicinal Diamines,r-Amino Ketones,and r-Amino Alcohols.J.Am.Chem.Soc,2005,127,5073
1.徐任生,叶阳,赵维民.天然产物化学导论,2005,73.
2.Joseph.P.Michael and David.Gravestock.Enaminones as intermediates in the synthesis of indojizidine alkaloids.Pure.Appl.Chem.1997,69,583.
3.Julien.Ceccon.;Andrew.E.Greene.;and Jean.-rancois.Poisson.asymmetric [2+2]cycloaddyion:tatal synthesis of(-)-Swainsonine and (+)-6-Epicastanospermine.Organic Letters.2006,8,4739.
4 Aronstam,R.S;Daly,S.W;Spande,T.F;Narayanan,T.K;Albuquerque,E.X.Neurochem Res.1986,11,1227.
5.Polniaszek,R.P;Belmont,S.E.J Org Chem.Enantioselective total syntheses of indolizidine alkaloids 167B and 209D.1990,55,4688.
6.Jefford,C.W;Tang,Q;Zaslona,A.Short,enantiogenic syntheses of (-)-indolizidine 167B and(+)-monomorine.J A Chem Soc.1991.113,3513.
7.Fleurant,A;Sliou,C;Celerier,J.P;Platzer,N;VuMoc,T;Lhommet,G.J.Heterocycl Chem.1995,32,255.
8 Joseph,P.M;David,G.Pure Appl Chem.1997,69,583.
9 Adrian L.Smith,Simon F.Williams,Andrew B.Holmes,Leslie R.Hughes,Colin Swithenbank,Zev Lidert.Stereoselective synthesis of(.+-.)-indolizidines 167B,205A,and 207A.Enantioselective synthesis of(-)-indolizidine 209B.J A Chem Soc.1988,110,8696
10 Andrew B.Holmes,Adrian L.Smith,Simon F.Williams,Leslie R.Hughes,Zev Lidert,Colin Swithenbank.Stereoselective synthesis of(.+-.)-indolizidines 167B,205A,and 207A.Enantioselective synthesis of(-)-indolizidine 209B.J Org Chem.1991,56,1393.
11.Cardilio,G.Chem Soc Rev.1996,25,117.
12.Franca M.Cordero,Alberto Brandi,Cecilia Querci,Andrea Goti,Francesco De Sarlo,Antonio Guarna.Rearrangement of isoxazoline-5-spiro derivatives.5. Diastereofacial selectivity in the cycloaddition of substituted five-membered cyclic nitrones and methylenecyclopropanes.Stereoselective synthesis of 3,5-substituted indolizidinones J Org Chem.1990,55,1762.
13 Organic Syntheses.1989,67,69.
14.Organic Syntheses.2002,79,154.
15.Ye,T;Mckervey,M.A.Organic Synthesis with.alpha.-Diazo Carbonyl Compounds.Chem Rev.1994,94,1091.
16.Doyle,M.P;Mckervey,M.A.J Chem Soc Chem Commun 1997,983.
17.Chen.F.M;Steinauer,R;Benoiton,N.L.Mixed anhydrides in peptide synthesis.Reduction of urethane formation and racemization using N-methylpiperidine as the tertiary amine base.J Org Chem 1983,48,2939.
18 Steven.Nahm.;Steven.M.Weinreb.N-methoxy-n-methylamides as effective acylating agents.Tetrahedron Lett.1981,22,3815.
19.James.McNulty.;Veronika.Grunner.;and Justin.Mao.Selective addition of Grignard reagents to 2,3-O-isopropylidene bis-Weinreb tartaric acid amide.Tetrahedron Lett.2001,42,5609.
20.Conrad,R.M;Grogan,M.J;Bertozzi,C.R.Stereoselective Synthesis of myo-Inositol via Ring-Closing Metathesis:A Building Block for Glycosylphosphatidylinositol(GPI)Anchor Synthesis.Org Lett.2002,4,1359.
21.Davis,F.A;Prasad,K.R;Nolt,M.B;Wu,Y.N-Sulfinyl β-Amino Weinreb Amides:Synthesis of Enantiopure β-Amino Carbonyl Compounds.Asymmetric Synthesis of(+)-Sedridine and(-)-Allosedridine.Org Lett.2003,5,925.
22.Ruiz,J;Sotomayor,N;Lete,E.Parham-Type Cycliacylation with Weinreb Amides.Application to the Synthesis of Fused Indolizinone Systems.Org Lett.2003,5,1115.
23.Organic Syntheses.1993,71,200.
24.Organic Syntheses.1986,64,1.
25.Daniel.L.C;Donald.H.L.Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates.Asymmetric syntheses of the quinolizidine alkaloids,(+)-myrtine,(-)-lasubine I,and(+)-subcosine I J Org Chem.1992,57,5807.
26.Markus,W;Waldemar,P;Dieter,S;Horst,K.Enantioselective syntheses of 2-Alkyl-,2,6-Dialkylpiperidines and Indolizidine alkaloids through diastereoselective Mannich-Michael reactions,synthesis.1997,1151.
1.徐任生,叶阳,赵维民.天然产物化学导论,2005,72.
2.Caroline.Roche.;Katan'na.Kadleci kova.;Amael.Veyron.;Philippe.Delair.;Christian.Philouze.;and Andrew.E.Greene.New Asymmetric Approach to Natural Pyrrolizidines:Synthesis of(+)-Amphorogynine A,(+)-Amphorogynine D,and(+)-Retronecine.J Org Chem.2005.70.8352.
3.Celia.Ribes.;Eva.Falomir.;Miguel.Carda.;and J.Alberto.Marco.Stereoselective Synthesis of the Glycosidase Inhibitor Australine through a One-Pot,Double-Cyclization Strategy.Organic Letters.2007.9.77
4.Yoshitaka.Ikeda.;Hikaru.Nonaka.;Tamotsu.Furumai.;and Yasuhiro.Igarashi.Cremastfine,a Pyrrolizidine Alkaloid from Cremastra appendiculata.J.Nat.Prod.2005,68,572-573.
5.Marc.Larcheveque.;Caroline.Sanner.;Robert.Azerad.;and Didier.Buission.The use of methyl substituted chiral synthons in the synthesis of pine sawflies pheromones.Tetrahedron,1988.44.6407.
6.Y.Le Merrer.;C.Gravier.;D.Languin-Micas.;J.C.Depezay.;Total synthesis of leukotriene(+)-LTB_4 from D-mannitol Tetrahedron Letters.1986.27.4161.
7.Bernard.L..Hirschbein,George M.Whitesides.Laboratory-scale enzymic/chemical syntheses of D-and L-.beta.-chlorolactic acid and D-and L-potassium glycidate.J A Chem Soc 1982,104,4458.
8.William R.Roush,Bradley B.Brown.Enantioselective synthesis of 2-alkyl-5-methylene-1,3-dioxolan-4-ones and exo-selective Diels-Alder reactions with cyclopentadiene.J Org Chem.1992.57.3380.
9.Takehisa.Kunieda.;Kenji.Koga.;and Shun-ichi.Yamada.Studies on optically active amino acids.Synthesis,resolution and racemization of bicyle α-Amino-ketones.Chem.Pharm.Bull.1967.15.337.
10.Shindo,M.;Sato,Y.;Shishido,K.A Novel Tandem[2+2]Cycloaddition-Dieckmann Condensation:Facile One-Pot Process To Obtain 2,3-Disubstituted-2-cycloalkenones from Ynolates.J A Chem Soc.1999.121.6507.
11.Deville,J.P.;Behar,V.Tandem Conjugate Cyanide Addition-Dieckmann Condensation in the Synthesis of the ABCD-Ring System of Lactonamycin Organic Letters.2002.4.1403.
12.Ho,J.Z.;Mohareb,R.M.;Ahn,J.H.;Sim,T.B.;Rapoport,H.Enantiospecific Synthesis of Carbapentostatins.J Org Chem.2003.68.109.
13.Peter W.K.Woo.Chiral synthesis of statine.Tetrahedron Letter.1985.26.2973.and references cited therein.
14.Daniel H.Rich,Eric T.Sun,Amrit S.Boparai Synthesis of (3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid derivatives.Analysis of diastereomeric purity.J Org Chem.1978.43.3624.
15.Kenneth E.Rittle,Carl F.Homnick,Gerald S.Ponticello,Ben E.Evans A synthesis of statine utilizing an oxidative route to chiral.alpha.-amino aldehydes.J Org Chem.1982.47.3016.
16.Francis M.F.Chen,Rene Stainauer,N.Leo Benoiton.Mixed anhydrides in peptide synthesis.Reduction of urethane formation and racemization using N-methylpiperidine as the tertiary amine base.J Org Chem.1983.48.2939.
17 Steven.Nahm.;Steven.M.Weinreb.N-methoxy-n-methylamides as effective acylating agents.Tetrahedron Lett.1981,22,3815.
18.James.McNulty.;Veronika.Grunner.;and Justin.Mao.Selective addition of Grignard reagents to 2,3-O-isopropylidene bis-Weinreb tartaric acid amide.Tetrahedron Lett.2001,42,5609.
19.Conrad,R.M;Grogan,M.J;Bertozzi,C.R.Stereoselective Synthesis of myo-Inositol via Ring-Closing Metathesis:A Building Block for Glycosylphosphatidylinositol(GPI)Anchor Synthesis Org Lett.2002,4,1359.
20.Davis,F.A;Prasad,K.R;Nolt,M.B;Wu,Y.N-Sulfinyl β-Amino Weinreb Amides:Synthesis of Enantiopure β-Amino Carbonyl Compounds.Asymmetric Synthesis of(+)-Sedridine and(-)-Allosedridine.Org Lett.2003,5,925.
21.Ruiz,J;Sotomayor,N;Lete,E.Parham-Type Cycliacylation with Weinreb Amides.Application to the Synthesis of Fused Indolizinone Systems.Org Lett.2003,5,1115.
2.O.P.Goel and U.Krolls,Org.Prep.Proced.Int,1987,19,75 and references cited therein
3.J.A.Fehrentz and B.Castro,Synthesis,1983,676.
4.I.Maugras,J.Poncet and P.Jouin,A synthetic approach to the plakoridines modeled on a biogenetic theory,Tetrahedron,1990,46,2807.
5.M.Braun and D.Waldmuller,Synthesis,1989,856.
6.D.T.Davies and P.J.Hanlon,Synth.Commun,1988,18,2273.
7.W.Oppolzer and A.F.Cunningham,Total synthesis of(±)chokol-A via an intramolecular type-Ⅰ-magnesium ene reaction.Tetrahedron Lett,1986 27,5467.
8.N.Irako,Y.Hamada and T.Shioiri,A new efficient synthesis of(S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine),the C-terminal unit of dolastatin.Tetrahedron,1992,48,7251.
9.Castro,B.;Dormoy,J.R.;Evin,G.;Selve,C.Zur cycloaddition von arylisocyanaten an ε-caprolactimather.Tetrahedron Lett.1975,14,1219.
10.Dormoy,J.R.;Castro,B.,The reaction of hexamethyl phosphoric triamide (HMPT)with phosphoryl chloride:A reexamination.Application to a novel preparation of BOP reagent for peptide coupling.Tetrahedron Lett.1979,20,3321.
11. Le-Nguyen, D.; Heitz, A.; Castro, B. J. Chem. Soc. Perkin Trans.I 1987,1915
12. Coste, J.; Le-Nguyen, D.; Castro, B. PyBOP~(?): A new peptide coupling reagent devoid of toxic by-product. Tetrahedron Lett. 1990,31,205.
13. Kahl, J. D. ; Greenberg, M. M. Introducing Structural Diversity in Oligonucleotides via Photolabile, Convertible C5-Substituted Nucleotides J.Am. Chem. Soc. 1999,121, 597.
14. Crowley, B. M. ; Mori, Y. ; McComas, C. C. ; Tang, D. ; Boger, D. L. Total Synthesis of the Ristocetin Aglycon. J.Am. Chem. Soc. 2004,126,4310.
15. You, S. -L. ; Kelly, J. W. The total synthesis of bistratamides F-I. Tetrahedron, 2005,61,241.
16. Lee, J.; Griin, J. H.; Nicas, T. I. Solid-Phase. Total Synthesis of Bacitracin A . J. Org. Chem. 1996, 61, 3983.
17. J. Einhorn, ; C. Einhorn and J. -L. Luche. A convenient method for the preparation of N-methoxyamides, Synth. Commun. 1990,20, 1105.
18. P. Kocienshi, M. Stocks,; D. Donald and M. Perry, Synlett, 1990 38
19. R. S. Garigipati, ; D. M. Tschaen and S. M. Weinreb, Total synthesis of (+)-actinobolin. J. Am. Chem. Soc, 1985,107, 7790.
20. D. A. Evans, ; S. J. Miller. ; M, D, Ennis and P. L. Ornstein, Asymmetric synthesis of macbecin I. J. Org. Chem. 1992, 57,1067
21. J. Michael. Williams. ;Ronald. B. Jobson.; Nobuyoshi. Yasuda.; George. Marc- hesini.; Ulf-H. Dolling and Edward. J. J. Grabowsk. A New General Method for Preparation of N.Methoxy-N-Methylamides. Application in Direct Conversion of an Ester to a Ketone. Tetrahedron Lett. 1995, 36, 5461.
22. Ashok. Rao. Tunoori. ; Jonathan. M. White and Gunda. I. Georg. A one-flask synthesis of Weinreb amides rom chiral and achiral carboxylic acids using the Deoxo-fluor luorinating reagent Organic Letters 2000,2,4091.
23. Miguel. A. Baile'n.; Rafael. Chinchilla.; David. J. Dodsworth and Carmen. Na'jera. Direct synthesis of hydroxamates from carboxylic acids using 2-mercaptopyridone-1-oxide-based thiouronium salts. Tetrahedron Lett. 2001, 42, 5013.
24 Jacqueline.C.S.Woo.;Erik.Fenster.;and Gregory.R.Dake.A Convenient Method for the Conversion of Hindered Carboxylic Acids to N-Methoxy-N-methyl (Weinreb)Amides.J.Org.Chem.2004,69,8984.
25.Carolyn.A.Leverett.;Michael.P.Cassidy and Albert.Padwa.Application of the Aza-Achmatowicz Oxidative Rearrangement for the Stereoselective Synthesis of the Cassia and Prosopis Alkaloid Family.J.Org.Chem.2006,71.8591.
26.Kavirayani.R.Prasad.and Pazhamalai.Anbarasan.An enantiospecific synthesis of(+)-hydroxy-exo-brevicomin.Tetrahedron Lett.2006,47,1433.
27.Kavirayani.R.Prasad.and Pazhamalai.Anbarasan.Stereoselective synthesis of (+)-boronolide and(-)-5-epi-boronolide.Tetrahedron Asymmetry 2006,17,1146.
28.Seung-Mann.Paek.;Seung-Yong,Seo.;Seok-Ho.Kim.;Jong-Wha.Jung.;Yong-Sil.Lee.;Jae-Kyung.Jung.and Young-Ger.Sub.Concise Syntheses of (+)-Macrosphelides A and B.Organic Letters.2005,7,3159.
29.Organic Syntheses.1993,8,68.
30.John.A.Murphy.;Aurelien.G.J.Commeureuc.;Thomas.N.Snaddon.;Thomas.M.McGuire.;Tanweer.A.Khan.;Kevin.Hisler.;Mark.L.Dewis.and Robert.Carling.Direct Conversion of N-Methoxy-N-methylamides (Weinreb Amides)to Ketones via a Nonclassical Wittig Reaction.Organic Letters.2005,7,1427.
31.Javier.Ruiz.;Nuria.Sotomayor.and Esther.Lete.Parham-Type Cycliacylation with Weinreb Amides.Application to the Synthesis of Fused Indolizinone Systems.Organic Letters.2003,5,1115.
32.Angel.Alberola.;Alfonso.Gonalez.Ortega.;M.Luisa.Sadaba.and Carmen.Sanudo.Versatility of Weinreb amides in the Knorr Pyrrole Synthesis.Tetrahedron.1999,55,6555.
33.Takashi.Ooi.;Mifune.Takeuchi.;Daisuke.Kato.;Yuldtaka.Uematsu.;Eiji.Tayama.;Daiki.Sakai.and Keiji.Maruoka.Highly Enantioselective Phase-Transfer-Catalyzed Alkylationof Protected r-Amino Acid Amides toward PracticalAsymmetric Synthesis of Vicinal Diamines,r-Amino Ketones,and r-Amino Alcohols.J.Am.Chem.Soc,2005,127,5073
1.徐任生,叶阳,赵维民.天然产物化学导论,2005,73.
2.Joseph.P.Michael and David.Gravestock.Enaminones as intermediates in the synthesis of indojizidine alkaloids.Pure.Appl.Chem.1997,69,583.
3.Julien.Ceccon.;Andrew.E.Greene.;and Jean.-rancois.Poisson.asymmetric [2+2]cycloaddyion:tatal synthesis of(-)-Swainsonine and (+)-6-Epicastanospermine.Organic Letters.2006,8,4739.
4 Aronstam,R.S;Daly,S.W;Spande,T.F;Narayanan,T.K;Albuquerque,E.X.Neurochem Res.1986,11,1227.
5.Polniaszek,R.P;Belmont,S.E.J Org Chem.Enantioselective total syntheses of indolizidine alkaloids 167B and 209D.1990,55,4688.
6.Jefford,C.W;Tang,Q;Zaslona,A.Short,enantiogenic syntheses of (-)-indolizidine 167B and(+)-monomorine.J A Chem Soc.1991.113,3513.
7.Fleurant,A;Sliou,C;Celerier,J.P;Platzer,N;VuMoc,T;Lhommet,G.J.Heterocycl Chem.1995,32,255.
8 Joseph,P.M;David,G.Pure Appl Chem.1997,69,583.
9 Adrian L.Smith,Simon F.Williams,Andrew B.Holmes,Leslie R.Hughes,Colin Swithenbank,Zev Lidert.Stereoselective synthesis of(.+-.)-indolizidines 167B,205A,and 207A.Enantioselective synthesis of(-)-indolizidine 209B.J A Chem Soc.1988,110,8696
10 Andrew B.Holmes,Adrian L.Smith,Simon F.Williams,Leslie R.Hughes,Zev Lidert,Colin Swithenbank.Stereoselective synthesis of(.+-.)-indolizidines 167B,205A,and 207A.Enantioselective synthesis of(-)-indolizidine 209B.J Org Chem.1991,56,1393.
11.Cardilio,G.Chem Soc Rev.1996,25,117.
12.Franca M.Cordero,Alberto Brandi,Cecilia Querci,Andrea Goti,Francesco De Sarlo,Antonio Guarna.Rearrangement of isoxazoline-5-spiro derivatives.5. Diastereofacial selectivity in the cycloaddition of substituted five-membered cyclic nitrones and methylenecyclopropanes.Stereoselective synthesis of 3,5-substituted indolizidinones J Org Chem.1990,55,1762.
13 Organic Syntheses.1989,67,69.
14.Organic Syntheses.2002,79,154.
15.Ye,T;Mckervey,M.A.Organic Synthesis with.alpha.-Diazo Carbonyl Compounds.Chem Rev.1994,94,1091.
16.Doyle,M.P;Mckervey,M.A.J Chem Soc Chem Commun 1997,983.
17.Chen.F.M;Steinauer,R;Benoiton,N.L.Mixed anhydrides in peptide synthesis.Reduction of urethane formation and racemization using N-methylpiperidine as the tertiary amine base.J Org Chem 1983,48,2939.
18 Steven.Nahm.;Steven.M.Weinreb.N-methoxy-n-methylamides as effective acylating agents.Tetrahedron Lett.1981,22,3815.
19.James.McNulty.;Veronika.Grunner.;and Justin.Mao.Selective addition of Grignard reagents to 2,3-O-isopropylidene bis-Weinreb tartaric acid amide.Tetrahedron Lett.2001,42,5609.
20.Conrad,R.M;Grogan,M.J;Bertozzi,C.R.Stereoselective Synthesis of myo-Inositol via Ring-Closing Metathesis:A Building Block for Glycosylphosphatidylinositol(GPI)Anchor Synthesis.Org Lett.2002,4,1359.
21.Davis,F.A;Prasad,K.R;Nolt,M.B;Wu,Y.N-Sulfinyl β-Amino Weinreb Amides:Synthesis of Enantiopure β-Amino Carbonyl Compounds.Asymmetric Synthesis of(+)-Sedridine and(-)-Allosedridine.Org Lett.2003,5,925.
22.Ruiz,J;Sotomayor,N;Lete,E.Parham-Type Cycliacylation with Weinreb Amides.Application to the Synthesis of Fused Indolizinone Systems.Org Lett.2003,5,1115.
23.Organic Syntheses.1993,71,200.
24.Organic Syntheses.1986,64,1.
25.Daniel.L.C;Donald.H.L.Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates.Asymmetric syntheses of the quinolizidine alkaloids,(+)-myrtine,(-)-lasubine I,and(+)-subcosine I J Org Chem.1992,57,5807.
26.Markus,W;Waldemar,P;Dieter,S;Horst,K.Enantioselective syntheses of 2-Alkyl-,2,6-Dialkylpiperidines and Indolizidine alkaloids through diastereoselective Mannich-Michael reactions,synthesis.1997,1151.
1.徐任生,叶阳,赵维民.天然产物化学导论,2005,72.
2.Caroline.Roche.;Katan'na.Kadleci kova.;Amael.Veyron.;Philippe.Delair.;Christian.Philouze.;and Andrew.E.Greene.New Asymmetric Approach to Natural Pyrrolizidines:Synthesis of(+)-Amphorogynine A,(+)-Amphorogynine D,and(+)-Retronecine.J Org Chem.2005.70.8352.
3.Celia.Ribes.;Eva.Falomir.;Miguel.Carda.;and J.Alberto.Marco.Stereoselective Synthesis of the Glycosidase Inhibitor Australine through a One-Pot,Double-Cyclization Strategy.Organic Letters.2007.9.77
4.Yoshitaka.Ikeda.;Hikaru.Nonaka.;Tamotsu.Furumai.;and Yasuhiro.Igarashi.Cremastfine,a Pyrrolizidine Alkaloid from Cremastra appendiculata.J.Nat.Prod.2005,68,572-573.
5.Marc.Larcheveque.;Caroline.Sanner.;Robert.Azerad.;and Didier.Buission.The use of methyl substituted chiral synthons in the synthesis of pine sawflies pheromones.Tetrahedron,1988.44.6407.
6.Y.Le Merrer.;C.Gravier.;D.Languin-Micas.;J.C.Depezay.;Total synthesis of leukotriene(+)-LTB_4 from D-mannitol Tetrahedron Letters.1986.27.4161.
7.Bernard.L..Hirschbein,George M.Whitesides.Laboratory-scale enzymic/chemical syntheses of D-and L-.beta.-chlorolactic acid and D-and L-potassium glycidate.J A Chem Soc 1982,104,4458.
8.William R.Roush,Bradley B.Brown.Enantioselective synthesis of 2-alkyl-5-methylene-1,3-dioxolan-4-ones and exo-selective Diels-Alder reactions with cyclopentadiene.J Org Chem.1992.57.3380.
9.Takehisa.Kunieda.;Kenji.Koga.;and Shun-ichi.Yamada.Studies on optically active amino acids.Synthesis,resolution and racemization of bicyle α-Amino-ketones.Chem.Pharm.Bull.1967.15.337.
10.Shindo,M.;Sato,Y.;Shishido,K.A Novel Tandem[2+2]Cycloaddition-Dieckmann Condensation:Facile One-Pot Process To Obtain 2,3-Disubstituted-2-cycloalkenones from Ynolates.J A Chem Soc.1999.121.6507.
11.Deville,J.P.;Behar,V.Tandem Conjugate Cyanide Addition-Dieckmann Condensation in the Synthesis of the ABCD-Ring System of Lactonamycin Organic Letters.2002.4.1403.
12.Ho,J.Z.;Mohareb,R.M.;Ahn,J.H.;Sim,T.B.;Rapoport,H.Enantiospecific Synthesis of Carbapentostatins.J Org Chem.2003.68.109.
13.Peter W.K.Woo.Chiral synthesis of statine.Tetrahedron Letter.1985.26.2973.and references cited therein.
14.Daniel H.Rich,Eric T.Sun,Amrit S.Boparai Synthesis of (3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid derivatives.Analysis of diastereomeric purity.J Org Chem.1978.43.3624.
15.Kenneth E.Rittle,Carl F.Homnick,Gerald S.Ponticello,Ben E.Evans A synthesis of statine utilizing an oxidative route to chiral.alpha.-amino aldehydes.J Org Chem.1982.47.3016.
16.Francis M.F.Chen,Rene Stainauer,N.Leo Benoiton.Mixed anhydrides in peptide synthesis.Reduction of urethane formation and racemization using N-methylpiperidine as the tertiary amine base.J Org Chem.1983.48.2939.
17 Steven.Nahm.;Steven.M.Weinreb.N-methoxy-n-methylamides as effective acylating agents.Tetrahedron Lett.1981,22,3815.
18.James.McNulty.;Veronika.Grunner.;and Justin.Mao.Selective addition of Grignard reagents to 2,3-O-isopropylidene bis-Weinreb tartaric acid amide.Tetrahedron Lett.2001,42,5609.
19.Conrad,R.M;Grogan,M.J;Bertozzi,C.R.Stereoselective Synthesis of myo-Inositol via Ring-Closing Metathesis:A Building Block for Glycosylphosphatidylinositol(GPI)Anchor Synthesis Org Lett.2002,4,1359.
20.Davis,F.A;Prasad,K.R;Nolt,M.B;Wu,Y.N-Sulfinyl β-Amino Weinreb Amides:Synthesis of Enantiopure β-Amino Carbonyl Compounds.Asymmetric Synthesis of(+)-Sedridine and(-)-Allosedridine.Org Lett.2003,5,925.
21.Ruiz,J;Sotomayor,N;Lete,E.Parham-Type Cycliacylation with Weinreb Amides.Application to the Synthesis of Fused Indolizinone Systems.Org Lett.2003,5,1115.