Journal of Organic Chemistry p. 3767 - 3774 (1985)
Update date:2022-07-29
Topics:
Dauben, William G.
Saugier, R. Kent
Fleischhauer, Ilona
A stereospecific synthesis of the basic crassin acetate nucleus, erythro-1-(hydroxymethyl)-14-hydroxy-4,8,12-trimethylcyclotetradeca-(E,E,E)-3,7,11-triene, has been achieved.Stereospecific syntheses of the two precursors to this ring system, (E,E)-3,7-dimethyl-9-(phenylthio)nona-3,7-dienal and (E)-2,8-bis(trimethylsiloxy)-2,7-dimethyloct-6-en-3-one, have been developed.These moieties were combined via an aldol condensation to yield erythro-9-hydroxy-10-<1-oxo-2-methyl-2-(trimethylsiloxy)propyl>-1-(phenylthio)-14-(trimethylsiloxy)-3,7,13-trimethyltetradeca-(E,E,E)-2,6,12-triene which, in a series of reactions, was cyclized to the titled 14-membered ring system.
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