Synthesis of 18-norandrosta-8,11,13-trienes from testosterone derivatives in methanoic acid
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1333-1336
- https://doi.org/10.1039/p19790001333
Abstract
Rearrangement of Δ9(11)-17α-methyltestosterone derivatives to 18-norandrosta-8,11,13-trienes occurs readily in boiling methanoic acid. Activation of the 14α-hydrogen in the thermodynamic enol may facilitate the aromatisation of ring c in the case of Δ6,9(11)-17α-methyltestosterone. 17α-Ethynyloestradiol similarly gives a perhydrochrysene derivative, but cyanohydrins derived from 17-ketones are resistant to rearrangement under these conditions.This publication has 4 references indexed in Scilit:
- Applications of high-potential quinones. Part 13. Dehydrogenation of de-A-estra-5,7,9-trienes to styrenesJournal of the Chemical Society, Perkin Transactions 1, 1979
- 18-Norpregna-8,11,13-trienes. Part 2. Preparation from 17β-methyl-17α-pregn-13-enesJournal of the Chemical Society, Perkin Transactions 1, 1978
- Anti-androgenic activity of 17,17-dimethyl-18-norandrost-13-enesSteroids, 1964
- The conversion of ergosterol to a ring c-benzenoid steroid by a selective aromatization reactionTetrahedron, 1964