Attempts to rearrange grandiflorenic acid [ent-kaura-9(11),16-dien-19-oic acid] to rings C/D analogues of antheridiogen (AAn) were unsuccessful. The norketones of grandiflorenic acid and the methyl ester underwent 10α→ 9α-methyl migration when treated with acetyl hypobromite, aqueous sulphuric acid, and bromine.
N. J. Lewis and J. MacMillan, J. Chem. Soc., Perkin Trans. 1, 1980, 1279 DOI: 10.1039/P19800001279
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