钌-SYNPHOS催化的不对称氢化反应：通向多拉贝利德A的C15-C30亚基高立体选择性合成的途径。

Ruthenium-SYNPHOS-catalyzed asymmetric hydrogenations: an entry to highly stereoselective synthesis of the C15-C30 subunit of dolabelide A.

作者信息

Roche Christophe, Desroy Nicolas, Haddad Mansour, Phansavath Phannarath, Genet Jean-Pierre

机构信息

Laboratoire de Synthèse Sélective Organique et Produits Naturels UMR 7573 CNRS, ENSCP, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 01, France.

出版信息

Org Lett. 2008 Sep 4;10(17):3911-4. doi: 10.1021/ol801493w. Epub 2008 Aug 6.

DOI:10.1021/ol801493w

PMID:18681446

Abstract

An efficient construction of the C15-C30 segment of the cytotoxic macrolide dolabelide A is described. The synthesis relies on ruthenium-SYNPHOS-mediated asymmetric hydrogenation reactions of beta-keto esters to generate the C19, C21, and C27 hydroxyl-bearing stereocenters with very high levels of enantio- and diastereoselectivity.

摘要

描述了细胞毒性大环内酯多拉贝德A的C15 - C30片段的高效构建。该合成依赖于钌 - SYNPHOS介导的β - 酮酯的不对称氢化反应，以非常高的对映选择性和非对映选择性生成带有C19、C21和C27羟基的立体中心。