A unified synthetic approach to trachylobane-, beyerane-, atisane- and kaurane-type diterpenes

被引：35

作者：

Abad, A ^{[1
]}

Agulló, C ^{[1
]}

Cuñat, AC ^{[1
]}

Marzal, ID ^{[1
]}

Navarto, I ^{[1
]}

Gris, A ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain

来源：

TETRAHEDRON | 2006年 / 62卷 / 14期

关键词：

terpenoids; Diels-Alder reaction; diazo compounds; ring opening; cyclopropane;

D O I：

10.1016/j.tet.2006.01.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general synthetic approach to the polycyclic carbon skeleton of biogenetically related trachylobane, beyerane, atisane, and kaurane diterpenes from carvone is described. The skeleton of these diterpenes is prepared from a common intermediate, that is, 25, readily prepared from carvone using an IMDA reaction and an intramolecular diazo ketone cyclopropanation of an unsaturated ketone as key steps. The tetracyclic diterpene ring systems are obtained from this key trachylobane-type intermediate through the regioselective reductive cleavage of the cyclopropane ring, after adequate modification of the functionalization around the tricyclo[3.2.1.0(2.7)] octane moiety. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3266 / 3283

页数：18

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