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Stereoselective Total Synthesis of Racemic (3S,4R/3R,4S)- and a Diastereoisomeric Mixture of (6E,10Z)-3,4,7,11-Tetramethyltrideca-6,10-dienal (Faranal); The Trail Pheromone of the Pharaoh's Ant

DOI: 10.1039/P19830001387

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1387 - 1393 (1983)

Update date:2022-08-11

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Authors:

Baker, RaymondBaker, Raymond

Billington, David C.Billington, David C.

Ekanayake, NeelakanthieEkanayake, Neelakanthie

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Article abstract of DOI:10.1039/P19830001387

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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Product name:CIS-3,4-DIMETHYLCYCLOPENTANONE

Cas No:19550-72-2

19550-72-2

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