巴弗洛霉素A1的c14 - c25亚基的合成。

Synthesis of the c14-c25 subunit of bafilomycin A1.

作者信息

Eustache Florence, Dalko Peter I, Cossy Janine

机构信息

Laboratoire de Chimie Organique associé au CNRS, ESPCI, 10 rue Vauquelin, 75231 Paris 05, France.

出版信息

J Org Chem. 2003 Dec 26;68(26):9994-10002. doi: 10.1021/jo035068m.

DOI:10.1021/jo035068m

PMID:14682693

Abstract

The enantioselective synthesis of the C14-C25 subunit of bafilomycin A1 was realized in a convergent route. The sequence involves two dynamic kinetic resolution steps of 2-alkyl 1,3-diketones that use optically active ruthenium complexes, an anti-selective reduction of a beta-hydroxyketone to control the C23 stereogenic center, and an aldol-type reaction under Evans' conditions, which sets the C17 and C18 stereogenic centers.

摘要

通过汇聚式路线实现了巴弗洛霉素A1的C14 - C25亚基的对映选择性合成。该序列包括使用光学活性钌配合物对2 - 烷基1,3 - 二酮进行的两个动态动力学拆分步骤、对β - 羟基酮进行的反选择性还原以控制C23手性中心，以及在埃文斯条件下进行的羟醛型反应，该反应确定了C17和C18手性中心。