Total Synthesis and Cytotoxicity of (+)-and (-)-Goniodiol and 6-epi-Goniodiol.Construction of alpha,beta-Unsaturated Lactones by Ring-Closing Metathesis

摘要

(+)-Goniodiol,a potent and selective cytotoxin,and (-)-6-epi-goniodiol,as well as their enantiomers,have been synthesized starting from cinnamyl alcohol.The key steps of the synthesis were Sharpless asymmetric epoxidation and cyclization of an acrylate derivative using ring-closing metathesis reaction.The cytotoxicity of both enantiomers of goniodiol and 6-epi-goniodiol against HL-60 cells was examined.