Enantioselective synthesis of herbertane sesquiterpenes:: synthesis of (-)-α-formylherbertenol

被引：18

作者：

Abad, A ^{[1
]}

Agulló, C ^{[1
]}

Cuñat, AC ^{[1
]}

Perni, RH ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(00)00079-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of 4-hydroxy-3-[(1S)-1,2,2-trimethylcyclopentyl]benzaldehyde [(-)-alpha-formylherbertenol 1], a herbertane-type sesquiterpene isolated from the leafy liverwort Herberta adunca, from beta-cyclogeraniol is described. The synthesis is based on the previously described preparation of an enantiopure 1,2,2-tri-methylcyclopentane synthon from which the characteristic aromatic moiety of 1 is elaborated, using a Robinson annulation and a palladium-catalysed methoxycarbonylation of an aryl triflate as key synthetic steps. The synthesis of the natural sesquiterpene (-)-alpha-herbertenol, also a natural sequiterpene, using the same methodology is also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1607 / 1615

页数：9

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