通过不对称的加氢甲酰化/大环化级联反应合成(+)-patulolide C。

Synthesis of (+)-patulolide C via an asymmetric hydroformylation/macrocyclization cascade.

机构信息

Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1322, USA.

出版信息

Org Lett. 2012 Feb 17;14(4):1180-2. doi: 10.1021/ol2034299. Epub 2012 Feb 3.

DOI:10.1021/ol2034299

Abstract

A highly atom-economical total synthesis of (+)-patulolide C has been accomplished in three steps from the known (2R)-8-nonyn-2-ol in 49% overall yield and 93% de. A Rh(I)-catalyzed asymmetric hydroformylation (AHF)/ intramolecular Wittig olefination cascade was utilized to set the C4-hydroxyl stereochemistry and E-olefin geometry as well as form the macrolactone.

摘要

（+）-巴图洛内酯 C 的高度原子经济性全合成已从已知的（2R）-8-壬炔-2-醇三步完成，总收率为 49%，立体选择性为 93%。采用 Rh（I）催化的不对称氢甲酰化（AHF）/分子内Wittig 烯烃加成级联反应来确定 C4-羟基的立体化学和 E-烯烃的几何构型，并形成大环内酯。