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Issue 0, 1966
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Constituents of Withania somnifera Dun. Part VII. Rearrangements in withaferin A

Abstract

The acid-catalysed rearrangement of the naturally occurring steroidal lactone withaferin A and of some of its derivatives has been investigated. Deoxy-dihydrowithaferin A undergoes a pinacol type rearrangement in which contraction of ring A takes place leading to an A-nor-5-formyl derivative. A similar rearranged product has been obtained by the catalytic hydrogenation of deoxy-dihydrowithaferin A. Under acidic conditions, withaferin A yields, by loss of one ring-A carbon atom, a 2,5-dien-1-one. The mass spectra of six significant compounds of this series are discussed.

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J. Chem. Soc. C, 1966, 1757-1764
Article type
Paper

Constituents of Withania somnifera Dun. Part VII. Rearrangements in withaferin A

D. Lavie, Y. Kashman, E. Glotter and N. Danieli, J. Chem. Soc. C, 1966, 1757
DOI: 10.1039/J39660001757

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