Synthesis and complete stereochemical assignment of psymberin/irciniastatin A

被引：88

作者：

Jiang, X ^{[1
]}

García-Fortanet, J ^{[1
]}

De Brabander, JK ^{[1
]}

机构：

[1] Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75390 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 32期

关键词：

D O I：

10.1021/ja0537068

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe a concise and flexible synthetic avenue for the preparation of compounds with structures relevant to those proposed for the novel marine-derived differential cytotoxins psymberin and irciniastatin A. Our efforts led to their complete stereochemical assignment and the notion that psymberin and irciniastatin A are identical compounds. Our total synthesis features an interesting termini-differentiating lactolization of a dialdehyde obtained from a C2-symmetrical bis-olefin precursor, a mild platinum-catalyzed hydrolysis of an epimerizable nitrile, a novel protocol to prepare sensitive methyl imidates, and a one-pot conversion of these imidates to N-acyl aminals. Starting from fragments 5-7 (prepared in 7-8 steps each, 30-49% overall yield) the synthesis of psymberin/irciniastatin A was completed in an additional 9 steps and 30% yield (17 steps longest linear sequence, 8.9% overall). Copyright © 2005 American Chemical Society.

引用

页码：11254 / 11255

页数：2

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