一种用于玫瑰嗜菌素的扩环方法。

A ring-expansion approach to roseophilin.

作者信息

Salamone Samuel G, Dudley Gregory B

机构信息

Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.

出版信息

Org Lett. 2005 Sep 29;7(20):4443-5. doi: 10.1021/ol051730k.

DOI:10.1021/ol051730k

PMID:16178554

Abstract

[reaction: see text] Preparation of a cyclopentenone-fused pyrrolophane, which serves as a model for the tricyclic core of roseophilin (1), is described. The synthetic scheme features a palladium-catalyzed annulation and oxidative cleavage sequence to provide a macrocyclic ketoester (17). Modified Paal-Knorr pyrrole synthesis and Friedel-Crafts acylation complete the pyrrolophane model system (20).

摘要

[反应：见正文] 描述了一种环戊烯酮稠合的吡咯并环烷的制备方法，该化合物作为玫瑰红菌素（1）三环核心的模型。合成方案的特点是钯催化的环化和氧化裂解序列，以提供大环酮酯（17）。改良的帕尔-克诺尔吡咯合成法和傅克酰基化反应完成了吡咯并环烷模型体系（20）的构建。