Diethyl Ether → 1-Hydroxydehydroepiandrosterone

Participants

Reaction Steps

Alkaline hydrogen peroxide epoxidation of androsta-1,4,6-triene-3,17-dione 17-ketal 1 with basic hydrogen peroxide yields the 1α,2α-epoxide 2. Treatment of 1α,2α-epoxyandrosta-4,6-dien-3,17-dione 17-ketal 2 with a large excess each of lithium metal and ammonium chloride in ammonia-tetrahydrofuran (1:1) under reflux leads to 1α,3β-dihydroxyandrost-5-en-17-one 17-ketal 3. Hydrolysis of the ketal affords 1α,3β-dihydroxyandrost-5-en-17-one, 4. Also, fermentation of DHEA with penicillium aspergillus affords 4, i.e. penicillium aspergillus may be able to 1α-hydroxylate other substrates. ##STR31## Dodson, R. M., Goldkamp, A. M., and Muir, R. D., JACS, 1957, 79, 3921. Dodson, R. M., Goldkamp, A. M., and Muir, R. D., JACS, 1960, 82, 4026.

Provenance & Evidence