碳水化合物衍生的α-烷氧基丙烯酸酯的关环复分解反应深入研究：DAH、KDO和2-脱氧-β-KDO的高效合成

An in-depth study on ring-closing metathesis of carbohydrate-derived alpha-alkoxyacrylates: efficient syntheses of DAH, KDO, and 2-deoxy-beta-KDO.

作者信息

Hekking Koen F W, Moelands Marcel A H, van Delft Floris L, Rutjes Floris P J T

机构信息

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

出版信息

J Org Chem. 2006 Aug 18;71(17):6444-50. doi: 10.1021/jo060913x.

DOI:10.1021/jo060913x

PMID:16901129

Abstract

Novel, efficient synthetic pathways to DAH, KDO, and 2-deoxy-beta-KDO are described. Ring-closing metathesis (RCM) of highly functionalized alpha-alkoxyacrylate fragments resulted in a series of synthetically versatile oxygen heterocyclic intermediates. Further functionalization of the resulting enol ether double bond and subsequent deprotection provided the natural products in high overall yields, starting from commercially available protected sugars.

摘要

本文描述了合成DAH、KDO和2-脱氧-β-KDO的新型高效合成途径。高度官能化的α-烷氧基丙烯酸酯片段的闭环复分解反应（RCM）产生了一系列具有多种合成用途的含氧杂环中间体。从市售的保护糖开始，所得烯醇醚双键的进一步官能化及随后的脱保护反应以较高的总产率得到了天然产物。