A Short, Stereoselective Route to 16α-(Substituted-alkyl)estradiol Derivatives

Thomas L. Fevig, John A. Katzenellenbogen

Research output: Contribution to journalArticlepeer-review


A variety of 16α-substituted 17β-estradiol derivatives can be prepared by a convenient two-step procedure: The lithium enolate of estrone 3-0-benzyl or 3-O-tert-butyldimethylsilyl ether undergoes clean, stereospecific alkylation with a variety of allylic, benzylic, or propargylic bromides (some bearing additional functionality) to furnish the 16α-substituted estrone ethers. Even with relatively bulky 16α-substituents, reduction of the C-17 ketone with lithium aluminum hydride proceeds with very high stereoselectivity to give the 16α-substituted 170-estradiol 3-O-ethers. This sequence provides ready access to a wide variety of 16α-functionalized estradiol derivatives.

Original languageEnglish (US)
Pages (from-to)247-251
Number of pages5
JournalJournal of Organic Chemistry
Issue number2
StatePublished - Jan 1 1987

ASJC Scopus subject areas

  • Organic Chemistry


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