作为N-酰基亚胺离子前体的N,N-缩醛：表喹酰胺的合成及绝对立体化学

N,N-acetals as N-acyliminium ion precursors: synthesis and absolute stereochemistry of epiquinamide.

作者信息

Wijdeven Marloes A, Wijtmans Roel, van den Berg Rutger J F, Noorduin Wim, Schoemaker Hans E, Sonke Theo, van Delft Floris L, Blaauw Richard H, Fitch Richard W, Spande Thomas F, Daly John W, Rutjes Floris P J T

机构信息

Radboud University Nijmegen, Institute for Molecules and Materials, Toernooiveld 1, NL-6525 ED Nijmegen, The Netherlands.

出版信息

Org Lett. 2008 Sep 18;10(18):4001-3. doi: 10.1021/ol801490m. Epub 2008 Aug 15.

DOI:10.1021/ol801490m

PMID:18702495

Abstract

A stereoselective synthesis of (+)-epiquinamide is presented in combination with determination of the absolute configuration of the natural product. Key steps in the sequence involved chemoenzymatic formation of an enantiomerically pure cyanohydrin, reductive cyclization to the corresponding cyclic N,N-acetal, and subsequent conversion into a suitable N-acyliminium ion precursor to enable construction of the second ring.

摘要

本文介绍了(+)-表奎宁酰胺的立体选择性合成方法，并确定了该天然产物的绝对构型。该合成路线的关键步骤包括对映体纯氰醇的化学酶法形成、还原环化生成相应的环状N,N-乙缩醛，以及随后转化为合适的N-酰基亚胺离子前体以构建第二个环。