Syntheses of oxygenated spongiane diterpenes from carvone.: Synthesis of dorisenone C

被引：8

作者：

Abad, A ^{[1
]}

Agulló, C ^{[1
]}

Cuñat, AC ^{[1
]}

García, AB ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2005年 / 61卷 / 08期

关键词：

terpene; spongiane; synthesis; carvone; Diels-Alder reaction; retro-ene reaction; propargylic ether;

D O I：

10.1016/j.tet.2005.01.012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of dorisenone C, a representative member of the spongiane-type diterpene family, is described. The synthesis follows a B --> AB --> ABC --> ABCD approach and is based on the initial preparation of the previously known hydroxy-aldehyde 14 (AB rings) from R-(-)-carvone, followed by an intramolecular Diels-Alder reaction between an oxygenated diene moiety and an acetylenic dienophile for the construction of the C ring (compound 22), and adequate manipulation of the Diels-Alder adduct functionality for completion of the spongiane framework. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1961 / 1970

页数：10

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