Stereoselective synthesis of polyoxygenated atisane-type diterpenoids

被引：19

作者：

Abad, A ^{[1
]}

Agulló, C ^{[1
]}

Cuñat, AC ^{[1
]}

Navarro, I ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, Burjassot, Spain

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 51期

关键词：

terpene; carvone; atisane; cyclopropanation; Diels-Alder reaction; radical cleavage;

D O I：

10.1016/S0040-4039(01)01953-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new stereoselective approach to polyoxygenated atisane-type diterpenes starting from (S)-(+)-carvone is described. The key steps involve an intramolecular Diels-Alder reaction. an unusual intramolecular diazo ketone cyclopropanation of an unsaturated ketone, and a regioselective endocyclic cleavage of a cyclopropyl carbinyl radical as key synthetic steps. The synthesis of the bioactive polyoxygenated atisanes atis-16(17)-en-3,14-dione (2) and 3R-hydroxy-atis-16(17)-en-2.14-dione (3) following this approach is presented. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8965 / 8968

页数：4

共 20 条

[1] Synthesis of terpenoid unsaturated 1,4-dialdehydes.: π-facial selectivity in the Diels-Alder reaction of the 1-vinyl-2-methylcyclohexene moiety of polycyclic systems with DMAD [J].