反式-2，5-二取代四氢呋喃的立体选择性和对映选择性合成
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摘要
血小板致活因子(PAF)是人体内受激细胞产生的血小板刺激剂，可导致炎症、溃疡等疾病。寻找PAF拮抗剂是国际医药界研究热点之一。天然的反式-2，5-二取代四氢呋喃的有疗效，但资源有限。现有的化学合成反式-2，5-二取代四氢呋喃的几条路线存在收率低，异构体难分离，或立体选择性不理想等缺点。高立体选择性合成反式-2，5-二取代四氢呋喃是期待解决的关键问题。本文独创新的合成方法：以(±)-乳醇，即(±)-4，10-二氧杂三环[5．2．1．0~(2,6)]-癸-8-烯-3-醇为原料，在其3-位和5-位先反向引入两个取代基，再经过热分解和催化加氢反应，高立体选择性地合成反式-2，5-二取代四氢呋喃。根据这个新方法，从(+)-乳醇或(-)-乳醇出发，经过加成、氧化、还原、热分解和催化加氢六步反应，对映选择性地合成了(2S，5S)-和(2R，5R)-2，5-二取代四氢呋喃，如旋光纯的MK-287和(2R，5R)-2-β-萘酚基-5-(3’，4’-二甲氧基苯基)四氢呋喃。并以(+)-乳醇为起始物，经过加成、甲基磺酰化、环合，热分解、氧化和还原六步反应，对映选择性地合成了脱氧维生素H的重要中间体(2S，3R，4S)-2-正戊基-3，4-二羟基四氢噻吩。为MK-287等PAF拮抗剂和维生素H等手性五员杂环类化合物等药物的合成，提供了新途径。
Platelet-Activating Factor (PAF) was discovered as a powerful platelet-stimulating agent which leads to some diseases, e.g. inflammation. Researching antagonists of platelet activating factor is one of the most important tasks of the medicine in the world today. Natural 2,5-disubstituted tetrahydrofiiran series ,whose resources are limited, were identified as competitive PAF-receptor antagonists. There are problems in some synthetic processes, for example, low yields, difficult separation of stereoisomers and /or poor stereoselectivity. The key problem is to synthesize high stereoselectively trans- 2,5- disubstituted tetrahydrofurans. This thesis sets up a new method to synthesize stereoselectively ?ra玸--2,5-disubstituted tetrahydrofurans by introducing two alkyl(aryl) groups in 3-C and 5-C of lactol, flash decomposition and hydrogenation. MK-287 analogues, (2S,5S) and (2R,5R)- trans-2,5-diaryl tetrahydrofurans, are synthesized enantioselectively by a serieous of reactions of addition, oxidation, addition, reduction, flash decomposition and hydrogenation from (-)-lactol or (+)-lactol . the optic purity of MK-287 is 100 %. (2S,3S,4R)-2-n- pentyl-3,4-dihydroxy tetrahydrothiofuran is synthesized from (+)-lactol by six steps: addition, sulfonylation by TsCl, cyclization, flash decomposition, oxidation and hydrogenation. This work present a new process to synthesize some chiral five-membre hetrocyclocompounds, such as MK-287, antagonists of
PAF, and biotin or deoxybiotin.
Platelet-Activating Factor (PAF) was discovered as a powerful platelet-stimulating agent which leads to some diseases, e.g. inflammation. Researching antagonists of platelet activating factor is one of the most important tasks of the medicine in the world today. Natural 2,5-disubstituted tetrahydrofiiran series ,whose resources are limited, were identified as competitive PAF-receptor antagonists. There are problems in some synthetic processes, for example, low yields, difficult separation of stereoisomers and /or poor stereoselectivity. The key problem is to synthesize high stereoselectively trans- 2,5- disubstituted tetrahydrofurans. This thesis sets up a new method to synthesize stereoselectively ?ra玸--2,5-disubstituted tetrahydrofurans by introducing two alkyl(aryl) groups in 3-C and 5-C of lactol, flash decomposition and hydrogenation. MK-287 analogues, (2S,5S) and (2R,5R)- trans-2,5-diaryl tetrahydrofurans, are synthesized enantioselectively by a serieous of reactions of addition, oxidation, addition, reduction, flash decomposition and hydrogenation from (-)-lactol or (+)-lactol . the optic purity of MK-287 is 100 %. (2S,3S,4R)-2-n- pentyl-3,4-dihydroxy tetrahydrothiofuran is synthesized from (+)-lactol by six steps: addition, sulfonylation by TsCl, cyclization, flash decomposition, oxidation and hydrogenation. This work present a new process to synthesize some chiral five-membre hetrocyclocompounds, such as MK-287, antagonists of
PAF, and biotin or deoxybiotin.
引文
1． Y. Ma, G. Q. Han, C. L. Li, Acta Pharmaceatica Sinica 1991, 26(5) :345-350．
2． Y. Ma, G. Q. Han, Y. Y. Wang, Acta Pharmaceatica Sinica 1993, 28 (5) : 370-373．
3． C.A. Demopoulos, R.N. Pinckard & D.J. Hanahan, J. Biol Chem. 1979, 9355-9358．
4． T.C. Lee, Platelet-Activating Factor and Related Lipid Mediators., ed. By F. Snyder, PP. 115-133, Plenum Press, New York, 1987．
5． J. Benveniste, P.M. Henson & C.G. Cochrane, J.Exp. Med. 1972, 136: 1356-1377．
6． M.C. Venuti, Annu. Rev. Med. Chem. 1985,20: 193-202．
7． A.-C. Rosam, J.L. Wallace & B.J.R. Whittle, Nature (London), 1986, 319: 54-56．
8． J. Benvenist & A. Arnoux. Platelet-Activating Factor and Structurally Related Ether-Lipids. Inserm Symposium no.23． Elsevier Science, Amsterdam, 1983．
9． B.B.vargaftig, J. Lefort, M. Chignard & J. Benveniste, Eur. J. Pharmacol . 1980,65:185-192．
10． M.L. Blank, F. Snyder, L.W. Byer , Biochem. Biophys, Res. Commum. 1979, 90: 1194-1200．
11． L.M.McManus, D.S.Hanahan, C.A.Demopoulos, J.Immund, 1980,124: 2919-2924．
12． M. Sanchez-Crespo, F. Alonoso, P. Inarrea. J. Immunopharma-cology, 1982, 4: 173-185．
13． T.W.Doebber,M.S.Wu & T.Y.Shen, Biochem. Biophys. Res. Commun, 1984,125: 980-987．
14． C.P. Page & J.Morley, Pharmacol. Research Commun. 1986,18:217-228．
15． J.Morley, C.P. Page & S.Sanjar, Int. Arch. Allergy Appl. Immunol 1985,77: 73-78．
16． E.Henocq & B.B.Vargaflig, Lancet,1986, ii: 1378-1385．
17． S.-B.Hwang, C-S.Lee, M.J.Cheah. & T.Y.Shen. Biochemistiy,l983, 22: 4756-4763．
18． F.H.Valone, E.Coles, V.R.Reinhol, J.Immunol, 1982, 129: 1637-1641．
19． F.H.Valone, & E J.Goetzl Immunology, 1983,48:141-149．
20． S.-B.Hwang, M.-H.Lam & T.Y.Shen, Biochem. Biophys, Res. Commun. 1985, 128:972-979．
21． S.-B.hwang, C.I.Li, M.-H. Lam,Lab. Invest. 1985,52:607-630．
22． S.-B.hwang,M.-H. Lam, & T.Y.Shen, Biochem. Biophys. Res. Commun. 1985, 128:972-979．
23． ZTerashita, S.Tsushima, Y.Yoshioka, Life Sci. 1983, 32: 1975-1982．
24． ZTerashita, Y.Imura, M.Takatani J. Pharmacol. Exp. Ther. 1987,242: 263-268．
25． T.Toyofuku, K.Kubo, T.Kobayashi. Prostaglandine 1986, 31: 271-281．
26． J.Casals-Stenzel, G.Muacevic. & K.-H. Weber. J. macol. Exp. Ther. 1987, 241: 974-981．
27． T.Biftu, N.F.Gamble, T.Doebber J. Med. Chem. 1986,29:1917-1921．
28． S.-B.Hwang, C.-S. Lee, M.J.Cheah, Biochemistry 1983,22:4756．
29． E.J.Corey, C.-P.Chen, M.J.Parry, Tetrahydron. Lett 1988,29(24) : 2899-2902．
30． S.-B.Hwang. M.-H.Lam, T,Bifiu,J. Bioloyical chem.,1985,260 (29) : 15639-15645．
31． M.M.Ponpipom, S.-B.Hwang, T.W.Doebbe, Biochem. & Biophy. Research Communications, 1988,150(3) : 1213-1220．
32． S.-B.Hwang, M.-H.Lam, A.W.Alberts,J. Pharmacol Exp. Ther. 1988, 246:534．
33． S.P.Sahoo, D.W.Graham, J.Acton, Bioorganic & Medicinal Chemictry Letters. 1991,1(2) :327-332．
34． J.C.Harmange, B.Figader, Tetrahydron: Asymmetry, 1993,4: 1711-1754
35． G.Cardillo, M.Orena, Tetrahedron. 1990,46: 3321．
36． H.Yoda,M.Mizutan & K.Takabe. Tetrahedron Letter, 1999,40:4701-47027．
37． Y.Shao .G.-K.Cao & S.-X. Pen. J. China Pharm. Univ. 1992,23(2) :65-70．
38． M.M.Ponpipom, B.Z.Yue, R.L.Bugianesi, Tetrahedron Lett. 1986,27:309．
39． B.M.Trist, J.L.Belletire ,S.Godleski, P.G.McDougal, J. Org. Chem, 1986, 51: 2370．
40． E.J.Cerey, R.K.Bakshi, S.Shibata. J. Am. Chem. Soc. 1987, 109: 7925-7927．
41． A.S.Thompson. D.M.Tslchaen, P.Simpson , Tetrahydron Lett. 1990, 31(48) :6953-6956．
42． E.J.Corey, B.B.Snider, J. Am. Chem. Soc. 1972, 94:2549．
43． R.C.Larick & W.H.Gony. J. Org. Chem, 1990, 55: 407-418．
44． F.Ozawa, Akubo & T.Hayashi, Tetrahydron Lett, 1992,33:1485-1488．
45． M.T.Reetz, K.Kesseler, Angew Chem. Int. Ed.,1983,22:989．
46． J.W.Cornforth, R.H.Cornforth and K.K.Mathew, J.Chem.Soc. 1959,112
47． G.E.Paeeis & E.C.Ashby. J. Am. Chem. Soc, 1971, 93: 1206．
48． E.C.Ashby, & M.B.Smith, J. Am. Chem. Soc, 1964, 86: 4363．
49． F.A.Carey. R.J.Sundberg. Advanced Organic Chemistry, Part B, Third Edition, De Boeck, P.368．
50． 大连工学院无机化学教研室，无机化学，人民教育出版社 , 1978, 434．
51． W.P.Griffith, S.V.Ley,Altrichim.Acta 1990,23: 13-19．
52． R.Bloch, C.Brillet, Synlett 1991,829-830．
53． E J.Corry and A. Palani, Tetrahedron Lett. 1995,36:3485．
54． C.Cimquin, I.Schaper, G.Mandville and R.Bloch,Synlett,1995 ,339．
55． C.S.Wilcow, M.D.Cowart, Carbohydr. Res .1987,171:141-160
56． M.D.Lewis, J.K.Cha, Y.Kishi, JAm.Chem.Soc. 1982,104:4976-4978．
57． J.M.Lanceliu, P.H.A.Zollo, P.Sinaij, Tetrahdron Lett, 1983, 24: 4833-4836．
58． G.A.Kraus, M.T.Molina, J.A.Walling, J.Org.Chem. 1987,52:1273-1276．
59． G.A.Kraus, M.T.Molina, J. Org. Chem.,1988, 53: 752-753．
60． A.Dondoni, A.Marra, M.C.Shermann, Tetrahedron Lett. 1993, 34: 7328-7326．
61． E.Ayali, S.Czernecki, J.Xiee, J.Chem, See. Chem. Commm, 1996,347-348．
62． W.Liu, J.A.Walker, J.J.Chen Tetrahedron Lett. 1996, 37: 5325-5328．
63． K Tanaka, M.Schionoya, J. Org. Chem. 1999, 64: 5002-5003．
64． J.Matulic-Adamic, L.Beigelman, Tetrahedron Lett. 1997, 38: 1669-1672．
65． H.Yoda, Y.Shimojo, K.Takabe, Synlett 1999,1969-1971．
66． T.K.M.Shing, J.G.Gillhouley, Tetrahedron 1994,50,8685-8698．
67． H.Yoda, M.Mizutani, K.Takabe. Tetrahedron Lett. 1999,40:4701-4702．
68． R.Blich, M.Bortolussi, C.Girard, M.Seck, Tetrahedron 1992,48: 453-462．
69． W.A.Pliskin & R.P.Eischens, Z.Phys.Chem., 1960,24:11．
70． B.D.Barford & R.R.Rye, J.Chem.Phys., 1974,60:1046．
71． E.W.Plummer & A.E.Bell, J.Vac.Sci. and Tech., 1972,9:583．
72． R.P.Eischens & W.A.Pliskin.Adv.Catalysis, 1958,10:26．
73． 金松寿等，有机催化,上海科学技术出版社，1986, 11．
74． O.Beek,Dis.Farday Soc. 1950,8:118．
75． R.Bloch, E.Guibe-Jampel and C.Giard, Tetrahedron Lett. 1985,26: 4085．
76． K.Matsuki, H.Inone and M.Takeda, Tetrahedron Lett.1993, 34: 1167．
77． H.Luna, K.Prasad and O.Repic, Tetrahedron: Asymmetry, 1994, 5:303．
78． J.G.Lee, HT.Cha, Tetrahedron Lett, 1992, 33(22) :3167-3168．
79． S.H.Korzeniowski, G.W.Gokel, Tetrahedron Lett. 1977,15(40) : 3519-3522．
80． H.Zollinger,"Azo and Diazo Chemistry",interscience, New York, 1961．
81． S.Patai, Ed,"The Chemistry of Diazonium and Diazo Groups", Part 2, pp.645-659, wiley,Bristol,1978．
82． W.A.Cowdrey and D.S.Davies, J.Chem. Soc.,Suppl, 1949,48．
83． A.S.Thompson, D.M.Tschaen, D.Simpson et al., J.Org.Chem. 1992,57,7044-7052．
84． H.A.Smith and W.C.Bedoit, Catalysts, 1953, 3:149．
85． P.E.Peterson and C.Casey, J.Org.Chem. 1964,29:2325．
86． K.Tayay Sci.Papers InsLPhsy.Chem.Res., Tokyo, 1952,56:285．
87． 张铸勇，祁国珍，庄莆，精细有机合成单元反应，华东化工学院出版社,197．
88． M.P.Doyle, B.Siegfried & J.F.Dellaria, J.Org.Chem. 1977,42(14) :2426-2430．
89． D.H.R.Barton,B.Lacher,S.Zard,Tetrahedron Lett.1985,26,5939-5942, D.H.R.Barton,D.Crich,G.Krestzchmar,J.C.S.Perkin Trans 1, 1986,39-53．
90． B.O.Lingred,T.Nilson,Acta Chem Scand 1973,27,888． A.B.Smith III,T.L.Leenay, J.Am.Chem.Soc. 1989,111:5761-5768．
91． D.H.R.Barton,B.Lacher,S.Zard,Tetrahedron 1987,43,4321-4328．
92． M.R.Uskokovic, Biotin In Encyclopedia of Chemical Technology; R.E.Kirk, D.E.Othmer, Eds; Wiley: New York, 1984, 24:41．
93． F.Kogl, B. Tennis, Z. Hoppe-Seyl, Physiol Chem. 1936,242:43．
94． V.duVigneaud, K.Hofmann, D.B.Melville, P.Gyorgy, J.Biol.Chem. 1941, 140:763．
95． V.duVigneaud, D.B. Melville, K.Fokkers, J.BioLChem. 1942,146:475．
96． J.Trotter, Y.A.Hamilton, Biochmistry, 1966, 5:713．
97． O.Hiroshi & ME.Sakae,Tetrahydron Lett,197516: 2765-2766．
98． M.Takahashi, Y.Shimakawa,日本公开特许公报, JP 62 169 777．
99． S.Ogino, S.Fujmoto, Y.Aoki, Agric. Biol. Chem., 1974,38: 275,707．
100． Y.Aoki, H.Suzuki, H.Akyama, Japan Kokai, 7487691,1974．
101． J.K.King & P. De Mayo, J.Chem. 1970, 48: 3704．
102． A. S. Thompson, D.M. Tschaen, P.Simpson, J.Org. Chem. 1992,57:7044-7052．
103． T.Biftu,S.-B. Hwang,T.W.Doebber, Eur.Pat.AppL EP.199 324; Chem. Abstre. 1987,106: 50026r
2． Y. Ma, G. Q. Han, Y. Y. Wang, Acta Pharmaceatica Sinica 1993, 28 (5) : 370-373．
3． C.A. Demopoulos, R.N. Pinckard & D.J. Hanahan, J. Biol Chem. 1979, 9355-9358．
4． T.C. Lee, Platelet-Activating Factor and Related Lipid Mediators., ed. By F. Snyder, PP. 115-133, Plenum Press, New York, 1987．
5． J. Benveniste, P.M. Henson & C.G. Cochrane, J.Exp. Med. 1972, 136: 1356-1377．
6． M.C. Venuti, Annu. Rev. Med. Chem. 1985,20: 193-202．
7． A.-C. Rosam, J.L. Wallace & B.J.R. Whittle, Nature (London), 1986, 319: 54-56．
8． J. Benvenist & A. Arnoux. Platelet-Activating Factor and Structurally Related Ether-Lipids. Inserm Symposium no.23． Elsevier Science, Amsterdam, 1983．
9． B.B.vargaftig, J. Lefort, M. Chignard & J. Benveniste, Eur. J. Pharmacol . 1980,65:185-192．
10． M.L. Blank, F. Snyder, L.W. Byer , Biochem. Biophys, Res. Commum. 1979, 90: 1194-1200．
11． L.M.McManus, D.S.Hanahan, C.A.Demopoulos, J.Immund, 1980,124: 2919-2924．
12． M. Sanchez-Crespo, F. Alonoso, P. Inarrea. J. Immunopharma-cology, 1982, 4: 173-185．
13． T.W.Doebber,M.S.Wu & T.Y.Shen, Biochem. Biophys. Res. Commun, 1984,125: 980-987．
14． C.P. Page & J.Morley, Pharmacol. Research Commun. 1986,18:217-228．
15． J.Morley, C.P. Page & S.Sanjar, Int. Arch. Allergy Appl. Immunol 1985,77: 73-78．
16． E.Henocq & B.B.Vargaflig, Lancet,1986, ii: 1378-1385．
17． S.-B.Hwang, C-S.Lee, M.J.Cheah. & T.Y.Shen. Biochemistiy,l983, 22: 4756-4763．
18． F.H.Valone, E.Coles, V.R.Reinhol, J.Immunol, 1982, 129: 1637-1641．
19． F.H.Valone, & E J.Goetzl Immunology, 1983,48:141-149．
20． S.-B.Hwang, M.-H.Lam & T.Y.Shen, Biochem. Biophys, Res. Commun. 1985, 128:972-979．
21． S.-B.hwang, C.I.Li, M.-H. Lam,Lab. Invest. 1985,52:607-630．
22． S.-B.hwang,M.-H. Lam, & T.Y.Shen, Biochem. Biophys. Res. Commun. 1985, 128:972-979．
23． ZTerashita, S.Tsushima, Y.Yoshioka, Life Sci. 1983, 32: 1975-1982．
24． ZTerashita, Y.Imura, M.Takatani J. Pharmacol. Exp. Ther. 1987,242: 263-268．
25． T.Toyofuku, K.Kubo, T.Kobayashi. Prostaglandine 1986, 31: 271-281．
26． J.Casals-Stenzel, G.Muacevic. & K.-H. Weber. J. macol. Exp. Ther. 1987, 241: 974-981．
27． T.Biftu, N.F.Gamble, T.Doebber J. Med. Chem. 1986,29:1917-1921．
28． S.-B.Hwang, C.-S. Lee, M.J.Cheah, Biochemistry 1983,22:4756．
29． E.J.Corey, C.-P.Chen, M.J.Parry, Tetrahydron. Lett 1988,29(24) : 2899-2902．
30． S.-B.Hwang. M.-H.Lam, T,Bifiu,J. Bioloyical chem.,1985,260 (29) : 15639-15645．
31． M.M.Ponpipom, S.-B.Hwang, T.W.Doebbe, Biochem. & Biophy. Research Communications, 1988,150(3) : 1213-1220．
32． S.-B.Hwang, M.-H.Lam, A.W.Alberts,J. Pharmacol Exp. Ther. 1988, 246:534．
33． S.P.Sahoo, D.W.Graham, J.Acton, Bioorganic & Medicinal Chemictry Letters. 1991,1(2) :327-332．
34． J.C.Harmange, B.Figader, Tetrahydron: Asymmetry, 1993,4: 1711-1754
35． G.Cardillo, M.Orena, Tetrahedron. 1990,46: 3321．
36． H.Yoda,M.Mizutan & K.Takabe. Tetrahedron Letter, 1999,40:4701-47027．
37． Y.Shao .G.-K.Cao & S.-X. Pen. J. China Pharm. Univ. 1992,23(2) :65-70．
38． M.M.Ponpipom, B.Z.Yue, R.L.Bugianesi, Tetrahedron Lett. 1986,27:309．
39． B.M.Trist, J.L.Belletire ,S.Godleski, P.G.McDougal, J. Org. Chem, 1986, 51: 2370．
40． E.J.Cerey, R.K.Bakshi, S.Shibata. J. Am. Chem. Soc. 1987, 109: 7925-7927．
41． A.S.Thompson. D.M.Tslchaen, P.Simpson , Tetrahydron Lett. 1990, 31(48) :6953-6956．
42． E.J.Corey, B.B.Snider, J. Am. Chem. Soc. 1972, 94:2549．
43． R.C.Larick & W.H.Gony. J. Org. Chem, 1990, 55: 407-418．
44． F.Ozawa, Akubo & T.Hayashi, Tetrahydron Lett, 1992,33:1485-1488．
45． M.T.Reetz, K.Kesseler, Angew Chem. Int. Ed.,1983,22:989．
46． J.W.Cornforth, R.H.Cornforth and K.K.Mathew, J.Chem.Soc. 1959,112
47． G.E.Paeeis & E.C.Ashby. J. Am. Chem. Soc, 1971, 93: 1206．
48． E.C.Ashby, & M.B.Smith, J. Am. Chem. Soc, 1964, 86: 4363．
49． F.A.Carey. R.J.Sundberg. Advanced Organic Chemistry, Part B, Third Edition, De Boeck, P.368．
50． 大连工学院无机化学教研室，无机化学，人民教育出版社 , 1978, 434．
51． W.P.Griffith, S.V.Ley,Altrichim.Acta 1990,23: 13-19．
52． R.Bloch, C.Brillet, Synlett 1991,829-830．
53． E J.Corry and A. Palani, Tetrahedron Lett. 1995,36:3485．
54． C.Cimquin, I.Schaper, G.Mandville and R.Bloch,Synlett,1995 ,339．
55． C.S.Wilcow, M.D.Cowart, Carbohydr. Res .1987,171:141-160
56． M.D.Lewis, J.K.Cha, Y.Kishi, JAm.Chem.Soc. 1982,104:4976-4978．
57． J.M.Lanceliu, P.H.A.Zollo, P.Sinaij, Tetrahdron Lett, 1983, 24: 4833-4836．
58． G.A.Kraus, M.T.Molina, J.A.Walling, J.Org.Chem. 1987,52:1273-1276．
59． G.A.Kraus, M.T.Molina, J. Org. Chem.,1988, 53: 752-753．
60． A.Dondoni, A.Marra, M.C.Shermann, Tetrahedron Lett. 1993, 34: 7328-7326．
61． E.Ayali, S.Czernecki, J.Xiee, J.Chem, See. Chem. Commm, 1996,347-348．
62． W.Liu, J.A.Walker, J.J.Chen Tetrahedron Lett. 1996, 37: 5325-5328．
63． K Tanaka, M.Schionoya, J. Org. Chem. 1999, 64: 5002-5003．
64． J.Matulic-Adamic, L.Beigelman, Tetrahedron Lett. 1997, 38: 1669-1672．
65． H.Yoda, Y.Shimojo, K.Takabe, Synlett 1999,1969-1971．
66． T.K.M.Shing, J.G.Gillhouley, Tetrahedron 1994,50,8685-8698．
67． H.Yoda, M.Mizutani, K.Takabe. Tetrahedron Lett. 1999,40:4701-4702．
68． R.Blich, M.Bortolussi, C.Girard, M.Seck, Tetrahedron 1992,48: 453-462．
69． W.A.Pliskin & R.P.Eischens, Z.Phys.Chem., 1960,24:11．
70． B.D.Barford & R.R.Rye, J.Chem.Phys., 1974,60:1046．
71． E.W.Plummer & A.E.Bell, J.Vac.Sci. and Tech., 1972,9:583．
72． R.P.Eischens & W.A.Pliskin.Adv.Catalysis, 1958,10:26．
73． 金松寿等，有机催化,上海科学技术出版社，1986, 11．
74． O.Beek,Dis.Farday Soc. 1950,8:118．
75． R.Bloch, E.Guibe-Jampel and C.Giard, Tetrahedron Lett. 1985,26: 4085．
76． K.Matsuki, H.Inone and M.Takeda, Tetrahedron Lett.1993, 34: 1167．
77． H.Luna, K.Prasad and O.Repic, Tetrahedron: Asymmetry, 1994, 5:303．
78． J.G.Lee, HT.Cha, Tetrahedron Lett, 1992, 33(22) :3167-3168．
79． S.H.Korzeniowski, G.W.Gokel, Tetrahedron Lett. 1977,15(40) : 3519-3522．
80． H.Zollinger,"Azo and Diazo Chemistry",interscience, New York, 1961．
81． S.Patai, Ed,"The Chemistry of Diazonium and Diazo Groups", Part 2, pp.645-659, wiley,Bristol,1978．
82． W.A.Cowdrey and D.S.Davies, J.Chem. Soc.,Suppl, 1949,48．
83． A.S.Thompson, D.M.Tschaen, D.Simpson et al., J.Org.Chem. 1992,57,7044-7052．
84． H.A.Smith and W.C.Bedoit, Catalysts, 1953, 3:149．
85． P.E.Peterson and C.Casey, J.Org.Chem. 1964,29:2325．
86． K.Tayay Sci.Papers InsLPhsy.Chem.Res., Tokyo, 1952,56:285．
87． 张铸勇，祁国珍，庄莆，精细有机合成单元反应，华东化工学院出版社,197．
88． M.P.Doyle, B.Siegfried & J.F.Dellaria, J.Org.Chem. 1977,42(14) :2426-2430．
89． D.H.R.Barton,B.Lacher,S.Zard,Tetrahedron Lett.1985,26,5939-5942, D.H.R.Barton,D.Crich,G.Krestzchmar,J.C.S.Perkin Trans 1, 1986,39-53．
90． B.O.Lingred,T.Nilson,Acta Chem Scand 1973,27,888． A.B.Smith III,T.L.Leenay, J.Am.Chem.Soc. 1989,111:5761-5768．
91． D.H.R.Barton,B.Lacher,S.Zard,Tetrahedron 1987,43,4321-4328．
92． M.R.Uskokovic, Biotin In Encyclopedia of Chemical Technology; R.E.Kirk, D.E.Othmer, Eds; Wiley: New York, 1984, 24:41．
93． F.Kogl, B. Tennis, Z. Hoppe-Seyl, Physiol Chem. 1936,242:43．
94． V.duVigneaud, K.Hofmann, D.B.Melville, P.Gyorgy, J.Biol.Chem. 1941, 140:763．
95． V.duVigneaud, D.B. Melville, K.Fokkers, J.BioLChem. 1942,146:475．
96． J.Trotter, Y.A.Hamilton, Biochmistry, 1966, 5:713．
97． O.Hiroshi & ME.Sakae,Tetrahydron Lett,197516: 2765-2766．
98． M.Takahashi, Y.Shimakawa,日本公开特许公报, JP 62 169 777．
99． S.Ogino, S.Fujmoto, Y.Aoki, Agric. Biol. Chem., 1974,38: 275,707．
100． Y.Aoki, H.Suzuki, H.Akyama, Japan Kokai, 7487691,1974．
101． J.K.King & P. De Mayo, J.Chem. 1970, 48: 3704．
102． A. S. Thompson, D.M. Tschaen, P.Simpson, J.Org. Chem. 1992,57:7044-7052．
103． T.Biftu,S.-B. Hwang,T.W.Doebber, Eur.Pat.AppL EP.199 324; Chem. Abstre. 1987,106: 50026r