Structure Revision of Poecillastrin C and the Absolute Configuration of the β-Hydroxyaspartic Acid Residue

Org Lett. 2017 Oct 6;19(19):5395-5397. doi: 10.1021/acs.orglett.7b02835. Epub 2017 Sep 28.

Abstract

The planar structure of poecillastrin C (1) was revised through selective reduction of the ester carbon. The absolute configuration of the β-hydroxyaspartic acid (OHAsp) residue was determined to be d-threo by Marfey's analysis. The acid hydrolysate of the reduction product of 1 liberated (2R,3R)-2-amino-3,4-dihydroxybutanoic acid, demonstrating that the β-carboxyl group in poecillastrin C was esterified. The structures of poecillastrins B-D and 73-deoxychondropsin A were also revised.

Publication types

  • Research Support, Non-U.S. Gov't