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

• DOI: 10.1021/acs.orglett.7b02835
• Publication Date: 2017-09-28T16:27:10Z
• Authors: Raku Irie; Kentaro Takada; Yuji Ise; Susumu Ohtsuka; Shigeru Okada; Kirk R. Gustafson; Shigeki Matsunaga
• Keywords: Absolute Configuration; Residue (chemistry); Absolute (philosophy)

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