Synthetic studies on clerodane diterpenoids. The total synthesis of (+/-)-2-oxo-5 alpha,8 alpha-13,14,15,16-tetranorclerod-3-en-12-oic acid

被引：18

作者：

Liu, HJ ^{[1
]}

Shia, KS ^{[1
]}

Han, YX ^{[1
]}

Sun, DQ ^{[1
]}

Wang, Y ^{[1
]}

机构：

[1] NATL TAIWAN UNIV,DEPT CHEM,TAIPEI 10764,TAIWAN

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1997年 / 75卷 / 06期

关键词：

cis-clerodanes; general synthetic approach; total synthesis; face-selective Diels-Alder reaction;

D O I：

10.1139/v97-079

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general synthetic approach to diterpenoids of the cis-clerodane family has been developed, leading to the first total synthesis, in racemic form, of 2-oxo-5 alpha,8 alpha-13,14,15,16-tetranorclerod-3-en-12-oic acid (2). The key operation involved is the face-selective Diels-Alder reaction of dienone ester 10 with trans-piperylene, giving rise to adduct 11 containing the decalin nucleus and correct stereogenic centers common to many cis-clerodane diterpenoids.

引用

页码：646 / 655

页数：10

共 54 条

[1] CONSTITUENTS OF SOLIDAGO SPECIES .4. SOLIDAGOIC ACIDS A AND B, DITERPENOIDS FROM SOLIDAGO-GIGANTEA VAR SEROTINA [J].