三氟甲磺酸铋催化的甾体激素 C17-二羟基丙酮侧链断裂直接转化为高官能化的 17-酮甾体激素。

Bismuth(III) triflate-catalyzed direct conversion of corticosteroids into highly functionalized 17-ketosteroids by cleavage of the C17-dihydroxyacetone side chain.

机构信息

Laboratório de Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, 3000-548, Coimbra, Portugal.

出版信息

J Org Chem. 2009 Nov 6;74(21):8488-91. doi: 10.1021/jo9018478.

PMID:19799442

Abstract

The use of bismuth(III) triflate as catalyst for the direct conversion of corticosteroids into highly functionalized 17-ketosteroids by cleavage of the C17-dihydroxyacetone side chain is reported. This catalytic process is very chemoselective, since functionalities of the starting corticosteroids, such as Delta(4)-3-keto, Delta(1,4)-3-keto, 11beta-hydroxyl, and 9beta,11beta-epoxide, remained intact.

摘要

报道了三氟甲磺酸铋(III)作为催化剂，用于通过 C17-二羟丙酮侧链的断裂，将皮质甾类化合物直接转化为高官能化的 17-酮甾类化合物。该催化过程具有非常好的化学选择性，因为起始皮质甾类化合物的官能团，如 Delta(4)-3-酮、Delta(1,4)-3-酮、11beta-羟基和 9beta,11beta-环氧化物，保持完整。