Labdane二萜“类天然产物”的合成研究
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摘要
以香紫苏内酯为原料,通过内酯开环、Kishner-Wolff-Huang还原等反应合成得到6个含有不同芳环的labdane二萜"类天然产物"1(a-c)和2(a-c),所得化合物经红外、质谱、1H NMR等表征。
Six labdane- like compounds 1( a- c) and 2( a- c) with different aryl groups were synthesized through lactone ring opening and Kishner- Wolff- Huang reduction starting from sclareolide. All the compounds obtained were characterized by IR,MS,and1 H NMR.
Six labdane- like compounds 1( a- c) and 2( a- c) with different aryl groups were synthesized through lactone ring opening and Kishner- Wolff- Huang reduction starting from sclareolide. All the compounds obtained were characterized by IR,MS,and1 H NMR.
引文
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[3]TAN D S.Diversity-oriented synthesis:exploring the intersections between chemistry and biology[J].Nat.Chem.Biol.2005,1(2):74-84.
[4]郭宗儒.天然产物的结构改造[J].化学进展,2012,47(2):144-157.
[5]周宇,张磊,栗增,等.高效合成技术在药物发中的应用[J].药学学报,2013,48(7):1014-1030.
[6]SCHREIBER S L.Target-oriented and diversity-ori ented organic synthesis in drug discovery[J].Science.2000,287:1964-1969.
[7]杨震.活性天然产物和结构多样性类天然产物的合成[J].化学进展,2009,21(1):47-54.
[8]刘钢,李裕林,南发俊.多样性导向的“类天然产物”化合物库合成[J].化学进展,2006,18(6):734-742.
[9]SHUL'TS E E,MIRONOV M E,KHARITONOV Y V.Furanoditerpenoids of the labdane seires:Occurrence in plants,total synthesis,several transformations and biological activity[J].Chem.Nat.Comp.2014,50(1):1-20.
[10]REUBEN J P.Two rings in them all:the labdanerelated diterpenoids[J].Nat.Prod.Rep.2010,27:1521-1530,and previous reviews in this series.
[11]HERSEL U,STECK M,SEIFERT K.A new route to 2,7-and 7-functionalized labdanes[J].Eur.J.Org.Chem,2000,(8):1609-1615.
[12]KOLYMPADI M,LIAPIS M,RAGOUSSIS V.Synthesis of the marine furanoditerpene(-)-Marginatone[J].Tetrahedron,2005,61(8):2003-2010.
[13]ZORETIC P A,FANG H,RIBEIRO A A.Application of a radical methodology toward the synthesis of d,1-5α-Pregnanes and related steroids:A stereoselective radical Cascade approach[J].J.Org.Chem.1998,63(21):7213-7217.
[14]JUSTICIA J,OLTRA J E,CUERVA J M.Palladium meddiated C-H activation in the field of terpenoids:synthesis of rostratone[J].Tetrahedron Lett,2004,45(22):4293-4296.
[15]JUSTICIA J,ROSALES A,BUNUEL E,el al.Titanocen ecatalyzed cascade cyclization of epoxypolyprenes:straightforward synthesis of terpenoids by free radical chemistry[J].Chem.Eur.J.2004,10(7):1778-1788.
[16]ZORETIC P A,FANG H.Synthesis of d,l-Norlabdane Oxide and Related Odorants:An Intramolecular Radical Approach[J].J.Org.Chem.1998,63(14):4779-4785.
[17]NAKANO C,HOSHINO T,SATO T,et al.Substrate specificity of the CYC2 enzyme from Kitasato spora griseola:production of sclarene,biformene,and novel bicyclic diterpenes by the enzymatic reactions of labdaneand halimane-type diter pene diphosphates[J].Tetrahedron Lett,2010,51(1):125-128.
[18]黄伟,王健波,唐功利.天然产物类药物的合成生物学研究[J].生命科学,2011,23(9):892-899.
[19]RAHEEM M A,NAGIREDDY J R,DURHAM R,et al.Efficient Procedure for the Preparation of 2-Bromofuran and Its Application in the Synthesis of 2-Arylfurans[J].Syn.Comm.2010,40:2138-2146.
[20]MARGAROS I,VASSILIKOGIANNAKIS G.Synthesis of Chinensines A-E[J].J.Org.Chem.2007,72:4826-4831.