First enantioselective synthesis of (-)-talaumidin, a neurotrophic diaryltetrahydrofuran-type lignan

被引：36

作者：

Esumi, Tomoyuki ^{[1
]}

Hojyo, Daisuke ^{[1
]}

Zhai, Haifeng ^{[1
]}

Fukuyama, Yoshiyasu ^{[1
]}

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Inst Pharmacognosy, Yamashiro, Tokushima 7708514, Japan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 24期

关键词：

D O I：

10.1016/j.tetlet.2006.04.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The first enantioselective total synthesis of a neurotrophic (-)-talaumidin (1) is described in 16 steps from 4-benzyloxy-3-methoxybenzaldehyde in ca. 10.7% overall yield, and thus has established the absolute configurations of the four stereogenic centers C-2 similar to C-5 of 1. The synthesis features the construction of the two successive chiral centers C-2 and C-3 by Evans asymmetric antialdol protocol as well as of the two chiral centers C-4 and C-5 in a highly stereocontrolled fashion by hydroboration/oxidation and epimerization, followed by Friedel-Crafts arylation. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3979 / 3983

页数：5

共 21 条

[1]

Stereocontrolled assembly of tetrasubstituted tetrahydrofurans: A concise synthesis of virgatusin [J].