Asymmetric Total Synthesis of Ieodomycin B.

ABSTRACT: Ieodomycin B, which shows in vitro antimicrobial activity, was isolated from a marine Bacillus species. A novel asymmetric total synthetic approach to ieodomycin B using commercially available geraniol was achieved. The approach involves the generation of 1,3-trans-dihydroxyl at C-3 and C-5 positions via a Crimmins-modified Evans aldol reaction and a chelation-controlled Mukaiyama aldol reaction of a p-methoxybenzyl-protected aldehyde, as well as the generation of a lactone ring in a deprotection-lactonization one-pot reaction.

SUBMITTER: Lin S 

PROVIDER: S-EPMC5295237 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature