Synthetic studies on electron transport inhibitors. Part 1. Chiral synthesis of a synthon for myxalamide D, piericidin A, and the actinopyrones
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 1901-1905
- https://doi.org/10.1039/p19910001901
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.Keywords
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