海螺环肽B和E的对映选择性全合成。

Enantioselective total synthesis of convolutamydines B and E.

作者信息

Nakamura Tomoaki, Shirokawa Shin-ichi, Hosokawa Seijiro, Nakazaki Atsuo, Kobayashi Susumu

机构信息

Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba, 278-8510, Japan.

出版信息

Org Lett. 2006 Feb 16;8(4):677-9. doi: 10.1021/ol052871p.

DOI:10.1021/ol052871p

PMID:16468740

Abstract

[reaction: see text] The first enantioselective total synthesis of convolutamydines B and E has been achieved using our vinylogous Mukaiyama aldol reaction. The synthesis features highly diastereoselective vinylogous Mukaiyama aldol reaction with isatin instead of aldehydes to construct a chiral center of convolutamydines. Additionally, the absolute configuration of natural convolutamydine B has been determined as R by its CD spectrum.

摘要

[反应：见正文] 使用我们的乙烯型 Mukaiyama 羟醛反应实现了海兔酰胺 B 和 E 的首次对映选择性全合成。该合成的特点是与异吲哚酮而非醛进行高度非对映选择性的乙烯型 Mukaiyama 羟醛反应，以构建海兔酰胺的手性中心。此外，通过圆二色光谱确定天然海兔酰胺 B 的绝对构型为 R。