Total Syntheses of Amphidinolides T1, T3, and T4

被引：22

作者：

Clark, J. Stephen ^{[1
]}

Romiti, Filippo ^{[1
]}

机构：

[1] Univ Glasgow, Sch Chem, WestCHEM, Glasgow G12 8QQ, Lanark, Scotland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 38期

关键词：

diazo ketone; natural products; oxidation; rearrangement; total synthesis; DIVERTED TOTAL-SYNTHESIS; CONCISE TOTAL-SYNTHESIS; ASYMMETRIC EPOXIDATION; STEREOSELECTIVE-SYNTHESIS; BIOACTIVE MACROLIDES; REARRANGEMENT; GENERATION; REDUCTION; OXIDATION; FRAGMENT;

D O I：

10.1002/anie.201305467

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Concise and high-yielding total syntheses of amphidinolides T1, T3, and T4 have been completed using an alkynyl macrolactone as a common late-stage intermediate. The required α-hydroxy ketone motif was installed by sequential alkyne hydrosilylation, epoxidation, and Fleming-Tamao oxidation. An oxonium ylide rearrangement formed the trisubstituted tetrahydrofuran core found in the natural products. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：10072 / 10075

页数：4

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