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Cyclization of isoprenoid compounds

Research paper by G. E. Muntyan, E. I. Mortikova, V. A. Smit, A. V. Semenovskii, V. F. Kucherov

Indexed on: 01 Aug '69Published on: 01 Aug '69Published in: Russian Chemical Bulletin



Abstract

The cyclization reaction of cis- and trans-1-(α-monocyclofarnesyl)-2-acetoxypropanes (IX) upon reaction with H2SO4 leads with good yield to 1-(cis-A/B-β-bicyclofarnesyl)-2-acetoxypropane (X) with an admixture (up to 20%) of theγ isomer (Xa). Upon carrying out this reaction with BF3 etherate the content of theγ-isomer in the mixture is increased to 50%.Under analogous conditions cyclization of cis- and trans-1-(β-monocyclofarnesyl)-2-acetoxypropanes (XI) proceeds more complexly and cannot serve as a preparative method of obtaining the corresponding bicyclic systems of the trans-decalin series.