Journal of the Chemical Society. Perkin transactions I p. 1387 - 1393 (1983)
Update date:2022-08-11
Topics:
Baker, Raymond
Billington, David C.
Ekanayake, Neelakanthie
Racemic (3S,4R/3R,4S)-faranal <(1a) + (1b)> has been synthesised by a convergent, stereospecific route which employed the addition of alkylcopper complexes to terminal acetylenes, to generate two trisubstituted double bonds, and a Diels-Alder reaction to establish the relative stereochemistry of the C-3, C-4 methyl groups.A diastereoisomeric mixture of faranals, enriched in the (3S,4S/3R,4R)-enantiomeric pair <(1c) + (1d)>, has been synthesised by a somewhat shorter route via an intermediate diester, obtained from electrochemical dimerisation of ethyl crotonate.
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