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轮环藤宁碱:绝对构型的阐明与全合成

Verticilide: elucidation of absolute configuration and total synthesis.

作者信息

Monma Souichi, Sunazuka Toshiaki, Nagai Kenichiro, Arai Takahiro, Shiomi Kazuro, Matsui Ryosuke, Omura Satoshi

机构信息

Kitasato Institute for Life Sciences and Graduate School of Infection Control Sciences, Kitasato University, Tokyo 108-8641, Japan.

出版信息

Org Lett. 2006 Nov 23;8(24):5601-4. doi: 10.1021/ol0623365.

Abstract

Verticilide (1) is a 24-membered cyclic depsipeptide isolated from the culture broth of Verticillium sp. FKI-1033. It inhibits ryanodine binding to ryanodine receptor (RyR) and has insecticidal activity. The stereochemistry of 2-hydroxyheptanoic acid in verticilide was elucidated by chiral HPLC analysis of the degradation product 6 and synthetic (+) and (-)-6. We also describe the practical total synthesis of verticilide. [reaction: see text].

摘要

轮枝菌素(1)是一种从轮枝菌属FKI-1033的培养液中分离得到的24元环缩肽。它能抑制ryanodine与ryanodine受体(RyR)的结合,并具有杀虫活性。通过对降解产物6以及合成的(+)-6和(-)-6进行手性高效液相色谱分析,阐明了轮枝菌素中2-羟基庚酸的立体化学结构。我们还描述了轮枝菌素的实用全合成方法。[反应:见正文]

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