对应重氮酰胺A核心亚基的四环缩醛胺的对映体控制合成。

Enantiocontrolled synthesis of a tetracyclic aminal corresponding to the core subunit of diazonamide A.

作者信息

Peris Gorka, Vedejs Edwin

机构信息

Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.

出版信息

J Org Chem. 2015 Mar 20;80(6):3050-7. doi: 10.1021/jo502939a. Epub 2015 Mar 5.

DOI:10.1021/jo502939a

PMID:25705992

Abstract

A chiral benzylic ether serves as an auxiliary for oxindole carboxylation (dr 5.2:1.0) that sets C10 configuration in a potential diazonamide precursor. The chiral substituent allows diastereomer separation and departs during a subsequent acid-catalyzed ring closure to form a tetracyclic aminal. With suitable N-protection, crystallization affords the aminal with 98-99% ee.

摘要

一种手性苄基醚用作氧化吲哚羧化反应的助剂（非对映体比例为5.2:1.0），该反应在潜在的重氮酰胺前体中设定C10构型。手性取代基允许非对映体分离，并在随后的酸催化闭环反应中离去，形成四环缩醛胺。通过适当的N-保护，结晶得到ee值为98-99%的缩醛胺。