Terpenoids: part LIII - synthesis of (+-)-gamma-cadinene

1970

BQ-SFB ENTOM-99 Project no.:10000094-1

E03151

The starting compound 2-isopropy1-4-carbethoxybutanal when subjected to wittig reaction with methallylidenetriphenylphosphorane affords 2-methyl-5-isopropyl-7-carbethoxy-1,3-hepta-diene, The resulting product on Diels-Alder reaction with ethyl acrylate yields1-methyl-4-carbethoxy-3-(1-isopropyl-3-carbethoxy-n-propy1)-cyclohex-1-ene. Cyclization of the diester followed by hydrolysis and decarboxylation gives 2-methyl-5-oxo-8-isopropyl-delta1-decalene which on wittig reaction with methylenetriphenylphosphorane furnishes (+-)-gamma-cadinene.

v.8(1):29-32, INDIAN JOURNAL OF CHEMISTRY (SECTION B: ORGANIC CHEMISTRY, INCLUDINGMEDICINAL CHEMISTRY)

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