Journal of the Chemical Society. Perkin transactions I p. 955 - 960 (1983)
Update date:2022-08-04
Topics:
Knight, David W.
Ojhara, Bol
A relatively short total synthesis of the true trail pheromone of Pharaoh's ant, (+/-)-faranal <(3SR,4RS)-(6E,10Z)-3,4,7,11-tetramethyltrideca-6,10-dienal (2)> is reported.The carbon skeleton was assembled by a Wittig condensation between (Z)-6-methyloct-5-en-2-one (4) and the 5-carboxypentylphosphonium salt (15).The ketone (4) was prepared in 'one-pot' and in a stereoselective manner using vinyl cuprate chemistry, while the relative stereochemistry of the two methyl substituents in the phosphonium salt (15) was established by using the Diels-Alder adduct (16) of buta-1,3-diene and maleic anhydride, which, after reduction and oxidative cleavage of the resulting cis-1,2-dimethylcyclohex-4-ene (18), gave only meso-3,4-dimethyladipic acid (19); this in turn was converted into the salt (15) in six straight-forward steps.
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Doi:10.1007/BF03170450
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(1982)
