Progress towards the total synthesis of aplyronine A

ORGN 416

Ahmad El-Awa, aelawa@purdue.edu, Mohammad Noshi, and Philip L Fuchs. Department of Chemistry, Purdue University, 560 Oval Drive, Box 397, BRWN BLDG, West Lafayette, IN 47907-1393
Cyclic epoxyvinyl sulfones are used as templates for the asymmetric synthesis of the three dipropionate units of Aplyronine A. Oxidative cleavage of the stereodefined stereotetrad units yield termini differentiated fragments that are advanced towards the assembly of Aplyronine A. Key reactions used in joining the smaller fragments together include Wadsworth-Emmons olefination and dianion alkylation.