Issue 0, 1979

Tetracyclic triterpenes. Part 2. A synthetic approach to cucurbitacins

Abstract

Efficient 19(10 9β) methyl migration leading to compounds with the cucurbitane skeleton occurs when 3β-acetoxy-9β,11β-epoxylanostan-7-one (1) is treated with boron trifluoride–diethyl ether in acetic anhydride. The major product (2) has the double bond in the 5,6-position which is common for natural cucurbitacins. The factors influencing the direction of the rearrangement are discussed. Several transformations including the removal of the 7-carbonyl group and epimerization of C-10 are described.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 1222-1227

Tetracyclic triterpenes. Part 2. A synthetic approach to cucurbitacins

Z. Paryzek, J. Chem. Soc., Perkin Trans. 1, 1979, 1222 DOI: 10.1039/P19790001222

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