Issue 0, 1973

Tetranortriterpenoids. Part XV. Base-induced fragmentation of some swietenine derivatives

Abstract

The swietenine derivatives (3), (9), and (22) are transformed under basic conditions, with rearrangement, into the acids (4), (10), and (23), respectively whose structures are supported spectroscopically and by mechanistically reasonable modes of formation. The rearrangements are initiated by β-dicarbonyl fission at C(2)–C(3)[or C(1)–C(2)] of the bicyclononane system of swietenine. Attention is drawn to the structural diversity and unpredictability of the products.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1973, 865-868

Tetranortriterpenoids. Part XV. Base-induced fragmentation of some swietenine derivatives

J. D. Connolly, R. Henderson, R. McCrindle, K. H. Overton and N. S. Bhacca, J. Chem. Soc., Perkin Trans. 1, 1973, 865 DOI: 10.1039/P19730000865

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