Total synthesis of 14α-hydroxyestrone 3-methyl ether
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 2830-2835
- https://doi.org/10.1039/p19790002830
Abstract
Total synthesis of 14α-hydroxyestrone 3-methyl ether (5) was achieved by the thermolysis of 2-[2-(1,2-dihydro-4-methoxybenzocyclobuten-1-yl)ethyl] 3-hydroxy-2-methyl-3-vinylcyclopentan-1-one (27), obtained by Grignard reaction of 2-[2-(1,2-dihydro-4-methoxybenzocyclobuten-1-yl)ethyl]-2-methylcyclopentane-1,3-dione (26) with vinylmagnesium bromide. An alternative synthesis of (5) started from authentic 14-dehydroestradiol bis(t-butyldimethylsilyl) ether (28) and proceeded through estradiol-14α,15α-epoxide 3-methyl 17β-t-butyldimethylsilyl bisether (31).This publication has 6 references indexed in Scilit:
- Asymmetric total synthesis of estradiol by an intramolecular cycloaddition of benzocyclobutene derivativeJournal of the American Chemical Society, 1978
- A Highly Stereoselective Synthesis of C(11)‐Functionalized Aromatic Steroids by an Intramolecular Benzocyclobutene‐Olefin ‐Cycloaddition. Preliminary CommunicationHelvetica Chimica Acta, 1977
- Studies on the syntheses of heterocyclic compounds. 675. A facile regiospecific and stereocontrolled synthesis of a diterpene alkaloid intermediate from benzocyclobutenesJournal of the American Chemical Society, 1976
- Syntheses of 15α-Hydroxyestrone and 15α-HydroxyestradiolCHEMICAL & PHARMACEUTICAL BULLETIN, 1975
- 14α-hydroxylation of oestrone by porcine adrenalsSteroids, 1968
- 14α-Hydroxyoestrone, a new oestrogen metaboliteBiochemical Journal, 1967