Cleavage of the C(20)–C(22) bond in a derivative of withanolide E (1), followed by oxidation, afforded the D-homoandrostane derivative (2), whose structure was determined by X-ray analysis; the mechanistic aspects of this unusual rearrangement are discussed.
D. Rabinovich, Z. Shakked, I. Kirson, G. Günzberg and E. Glotter, J. Chem. Soc., Chem. Commun., 1976, 461 DOI: 10.1039/C39760000461
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