A New Synthesis of (+/-)-5,6-Dehydrosenedigitalene
Ethyl 2-carbethoxy-5-oxohexanoate (II) on heating with NaCl in DMSO-water mixture gives the monoester (III) which when submitted to selective Grignard reaction with p-tolylmagnesium bromide furnishes ethyl 5-hydroxy-5-(p-tolyl)hexanoate (IV).The benzylic alcohol (IV) on catalytic hydrogenolysis gives ethyl 5-(p-tolyl)hexanoate (V) which on reduction with LAH provides the alcohol (VI).Oxidation of VI with Corey's reagent furnishes the aldehyde (VII) which on Wittig reaction with methylenetriphenylphosphorane in DMSO yields the title compound (I).
Vig, O. P.,Sharma, M. L.,Verma, N. K.
p. 384 - 385
(2007/10/02)
REACTION OF CHLOROMETHYLCARBENE WITH TRIMETHYLSILYL ENOL ETHERS. SYNTHESIS OF EUCARVONE, (+/-)-NUCIFERAL AND (+/-)-MANICONE.
New synthesis of Eucarvone 7, (+/-)-Nuciferal 12 and (+/-)-Manicone 16 are described from trimethylsilyl enol ethers 2, 10 and 14 via their chloromethylenation products by means of a two carbons homologation reaction.
Blanco, L.,Slougui, N.,Rousseau, G.,Conia, J. M.
p. 645 - 648
(2007/10/02)
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