A STEREOSPECIFIC FORMAL SYNTHESIS OF CLAVULONES FROM TRICYCLO[5.2.1.0(2,6)]DECADIENONE EPOXIDES

被引：34

作者：

KLUNDER, AJH

ZWANENBURG, B

LIU, ZY

机构：

[1] CATHOLIC UNIV NIJMEGEN,DEPT ORGAN CHEM,6525 ED NIJMEGEN,NETHERLANDS

[2] CHINESE ACAD SCI,SHANGHAI INST ORGAN CHEM,SHANGHAI 200032,PEOPLES R CHINA

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 26期

关键词：

D O I：

10.1016/0040-4039(91)80708-E

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereospecific formal synthesis of clavulones 1, prostanoids of marine origin, has been accomplished starting from tricyclo[5.2.1.0(2,6)]decadienone epoxide 2. Reaction with oct-2-ynyl zinc bromide, followed by reductive epoxide ring opening and subsequent thermal cycloreversion, using flash vacuum thermolysis, leads to gamma-hydroxycyclopentenone 9, an essential builing block for clavulones I and II, in an excellent overall yield.

引用

页码：3131 / 3132

页数：2

共 11 条

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