Total synthesis of d,l-isospongiadiol: An intramolecular radical cascade approach to furanoditerpenes

被引：33

作者：

Zoretic, PA ^{[1
]}

Wang, M ^{[1
]}

Zhang, YZ ^{[1
]}

Shen, ZQ ^{[1
]}

Ribeiro, AA ^{[1
]}

机构：

[1] DUKE UNIV,MED CTR,DUKE NMR SPECT CTR,DURHAM,NC 27710

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 05期

关键词：

D O I：

10.1021/jo951581r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective oxidative free-radical cyclization of beta-keto ester polyenes 7 and 19 has been accomplished as a one-step entry to the tricarbocyclic synthons 8 and 21 which contain five and six stereogenic centers, respectively. These key synthons possessing an axial carboethoxy group at C-4 were ultimately converted to the spongian skeleton (8 --> 14 and 21 --> 25 --> 14). The synthesis of d,l-isospongiadiol (3) from the common intermediate 14 was realized after introduction of the 2 alpha-hydroxy group in the spongian A-ring via epoxidation of silyl enol ether 28 and subsequent desilylation.

引用

页码：1806 / 1813

页数：8

共 27 条

[1]

CAPELLE N, 1980, B SOC CHIM BELG, V89, P399

[2]

CHAUDHARY SK, 1979, TETRAHEDRON LETT, P99

[3] NEW RADICAL-MEDIATED POLYOLEFIN CYCLIZATIONS DIRECTED TOWARDS STEROID RING SYNTHESIS [J].