Enantioselective synthesis and absolute configurations of aculeatins A, B, D, and 6-epi-aculeatin D

被引：41

作者：

Alvarez-Bercedo, Paula

Falomir, Eva ^{[1
]}

Carda, Miguel

Marco, J. A.

机构：

[1] Univ Jaume 1, Depart Q Inorgan & Organ, E-12080 Castellon de La Plana, Spain

[2] Univ Valencia, Depart Q Organ, E-46100 Burjassot, Valencia, Spain

来源：

TETRAHEDRON | 2006年 / 62卷 / 41期

关键词：

aculeatins; absolute configuration; asymmetric allylation; aldol reaction; remote induction; spiroacetals; hypervalent iodine; oxidative spiroacetalization;

D O I：

10.1016/j.tet.2006.07.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The three naturally occurring, bioactive spiroacetals aculeatins A, B, and D, as well as the non-natural 6-epi-aculeatin D have been synthesized for the first time in enantiopure form using an asymmetric allylation as the only chirality source. A further key step was a stereo-selective aldol reaction with remote induction. The absolute configurations of the natural products have been established and an erroneous structural assignment has been corrected. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：9641 / 9649

页数：9

共 40 条

[1]

[Anonymous], 1997, ORG REACT

[2] Biomimetic synthesis of (±)-aculeatin D [J].