Diastereoselective synthesis of spongian diterpenes.: Total synthesis of the furanoditerpene (-)-spongia-13(16),14-diene.

被引：21

作者：

Arnó, M ^{[1
]}

González, MA ^{[1
]}

Zaragozá, RJ ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1999年 / 55卷 / 42期

关键词：

marine metabolites; synthesis; furanoditerpenes; sponges;

D O I：

10.1016/S0040-4020(99)00725-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An effective diastereoselective synthesis of the marine-sponge metabolite (-)-spongia-13(16),14-diene 1 is achieved starting from S-(+)-carvone via a homochiral phenanthrenone as the key intermediate for the construction of the furan ring system. S-(+)-Carvone was transformed into the phenanthrenone 2a in six steps (53% overall yield), using an intramolecular Diels-Alder reaction as the key step. Conversion of the enone function in 2a into an epoxyaldehyde function followed by cyclisation and aromatisation in acid conditions completed the construction of ring D. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：12419 / 12428

页数：10

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