Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi-Sakurai reaction

Chem Commun (Camb). 2016 Sep 14;52(71):10747-50. doi: 10.1039/c6cc05747k. Epub 2016 Aug 10.

Abstract

The synthesis of dehaloperophoramidine, a non-halogenated derivative of the marine natural product perophoramidine, and its biological activity towards HCT116, HT29 and LoVo colorectal carcinoma cells is reported. A [3,3]-Claisen rearrangement and an epoxide opening/allylsilylation reaction installed the contiguous all-carbon quaternary stereocentres with the required relative stereochemistry.