Steroids and Related Natural Products. VII. Boron Trifluoride Etherate-Lithium Aluminum Hydride Reduction of Smilagenin Acetate

George R. Pettit, T. R. Kasturi

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

Reduction of smilagenin acetate (Va) using a boron trifluoride etherate-lithium aluminum hydride reagent, followed by hydrogen peroxide oxidation and acetylation, was found to yield: 3±-ethoxysmilagenin (Vb), 3²-ethoxydihydrosmilagenin acetate (Via), dihydrosmilagenin diacetate (VIb), and a complex mixture of partially acetylated products. Similar reaction conditions were employed to convert dihydrodiosgemn (II) to dihydrochlorogenin (III). Boron trifluoride etherate-lithium aluminum hydride reduction of 3²-acetoxy-5±-cholestane and 3²:-acetoxy-5a-Ianostane (Villa) was shown to yield the corresponding 3²-ethoxy (e.g., VTIIb) derivatives.

Original languageEnglish (US)
Pages (from-to)4553-4556
Number of pages4
JournalJournal of Organic Chemistry
Volume26
Issue number11
DOIs
StatePublished - Nov 1961
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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