The synthesis of 10-hydroxy-10α-testosterone

F. Sondheimer, R. Mechoulam, M. Sprecher

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

The degradation of 19-norandrost-4-ene-3,17-dione (IV) to the tricyclic diketo-ester (I) is described. Michael condenstaion between I and methyl vinyl ketone in ethanolic sodium ethoxide yielded the 10α-carbomethoxy-ketol (XVIIIa), as well as the 10α-carboethoxy-ketol (XVIIIb). Dehydration of these ketols led to the corresponding Δ4-3-ones (XIXa and XIXb), respectively. Reduction of either XIXa or XIXb with LiAlH4 and subsequent oxidation with MnO2 furnished 19-hydroxy-10α-testosterone (XXIIIa).

Original languageEnglish
Pages (from-to)2473-2485
Number of pages13
JournalTetrahedron
Volume20
Issue number11
DOIs
StatePublished - 1964
Externally publishedYes

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