对（-）-α- kainic 酸的对映选择性全合成。

Enantioselective total synthesis of (-)-alpha-kainic acid.

机构信息

Organisch-Chemisches Institut der Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany.

出版信息

Org Lett. 2010 Mar 5;12(5):1108-11. doi: 10.1021/ol1001076.

DOI:10.1021/ol1001076

PMID:20148523

Abstract

An enantioselective total synthesis of (-)-alpha-kainic acid is described. Key steps are an Ir-catalyzed allylic amination with a propargylic amine to provide an enyne and a diastereoselective intramolecular Pauson-Khand reaction. Subsequent steps involve a Baeyer-Villiger reaction, reduction of the resulting lactone, and direct Jones oxidation of a silyl ether.

摘要

描述了（-）-alpha- kainic 酸的对映选择性全合成。关键步骤是 Ir 催化的烯丙基胺与炔丙基胺的加成反应，得到烯炔，以及非对映选择性的 Pauson-Khand 反应。随后的步骤包括 Baeyer-Villiger 反应、生成的内酯的还原，以及硅醚的直接琼斯氧化。