Asymmetric synthesis of double bond isomers of the structure proposed for pyrinodemin A and indication of its structural revision

Abstract

Asymmetric synthesis of double bond isomers (+)-2 (Δ 15′,16′) and (+)-3 (Δ 14′,15′) of the structure (1) (Δ 16′,17′) proposed for pyrinodemin A, a cytotoxic bis-pyridine alkaloid with a unique cis-cyclopent[c]isoxazolidine moiety from a marine sponge, has been accomplished. Pyrinodemin A was indicated to be a 1:1 racemic mixture of 2 from comparison of C18 and chiral HPLC analysis for pyrinodemin A and the synthetic compounds as well as ESIMS data of oxidative degradation products of pyrinodemin A. © 2005 by MDPI.