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)
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