A formal synthesis of (-)-mycalamide A

被引：54

作者：

Trost, BM ^{[1
]}

Yang, HB ^{[1
]}

Probst, GD ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 01期

关键词：

D O I：

10.1021/ja038787r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Novel strategies are developed for an efficient formal synthesis of (-)-mycalamide A. The left-hand side (-)-7-benzoylpederic acid is synthesized from (2S,3S)-2,3-epoxybutane. The key features include a highly regioselective Ru-catalyzed alkene-alkyne coupling reaction and a novel way to control the challenging C(7) stereocenter. The right-hand side was synthesized from (R)-pantolactone. The complex trioxodecalin core is constructed with two Pd(0)-catalyzed O-π-allyl cyclizations. The first one is chemoselective, while the second one is highly diastereoselective. Three additional steps would be required to complete a total synthesis of (-)-mycalamide A. Copyright © 2004 American Chemical Society.

引用

页码：48 / 49

页数：2

共 42 条

[1] CARBOHYDRATE TRIFLATES - REACTION WITH NITRITE, LEADING DIRECTLY TO EPI-HYDROXY COMPOUNDS [J].