Synthetic studies on electron transport inhibitors. Part 1. Chiral synthesis of a synthon for myxalamide D, piericidin A, and the actinopyrones

Abstract

The trimethylsilyl enolate 9 of (1′R,2′S)-N-methylephedrine propionate was condensed with tiglic aldehyde to afford the (1′R,2′S,2S,3R)-ester 10 with high stereoselectivity; conversion into the aldehyde 12 was effected without epimerisation; and the sequence 12→13→15→19→20 afforded in 84% e.e. the (+)-(4R,5R,2E,6E)-sulphone 20, a synthon for the electron transport inhibitors piericidin A 2 and myxalamide D 4, as well as the actinopyrones 5.