Total Syntheses of Bryostatins: Synthesis of Two Ring-Expanded Bryostatin Analogues and the Development of a New-Generation Strategy to Access the C7-C27 Fragment

被引：23

作者：

Trost, Barry M. ^{[1
]}

Yang, Hanbiao ^{[1
]}

Dong, Guangbin ^{[1
]}

机构：

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 35期

关键词：

bryostatins; domino reactions; metathesis; palladium; ruthenium; ANTINEOPLASTIC AGENTS; CLOSING METATHESIS; SELECTIVE METHOD; ASYMMETRIC-SYNTHESIS; CATALYZED REACTIONS; CARBOXYLIC ESTERS; C-C; EFFICIENT; BRYOZOAN; ALCOHOLS;

D O I：

10.1002/chem.201002932

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report the synthesis of novel ring-expanded bryostatin analogues. By carefully modifying the substrate, a selective and high-yielding Ru-catalyzed tandem enyne coupling/Michael addition was employed to construct the northern fragment. Ring-closing metathesis was utilized to form the 31-membered ring macrocycle of the analogue. These ring-expanded bryostatin analogues possess anticancer activity against several cancer cell lines. Given the difficulty in forming the C16-C17 olefin at a late stage, we also describe our development of a new-generation strategy to access the C7-C27 fragment, containing both the ring B and C subunits.

引用

页码：9789 / 9805

页数：17