Steroids and related natural products. VII. Boron trifluoride etherate-lithium aluminum hydride reduction of smilagenin acetate

George Pettit, T. R. Kasturi

Research output: Contribution to journalArticle

16 Citations (Scopus)

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: 3β-ethoxysmilagenin (Vb), 3β-ethoxydihydrosmilagenin acetate (VIa), dihydrosmilagenin diacetate (VIb), and a complex mixture of partially acetylated products. Similar reaction conditions were employed to convert dihydrodiosgenin (II) to dihydrochlorogenin (III). Boron trifluoride etherate-lithium aluminum hydride reduction of 3β-acetoxy-5α-cholestane and 3β-acetoxy-5α-lanostane (VIIIa) was shown to yield the corresponding 3β-ethoxy (e.g., VIIIb) derivatives.

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

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Biological Products
Acetates
Steroids
Cholestanes
Acetylation
Complex Mixtures
Hydrogen Peroxide
Derivatives
Oxidation
boron trifluoride etherate
lithium aluminum hydride
sarsasapogenin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Steroids and related natural products. VII. Boron trifluoride etherate-lithium aluminum hydride reduction of smilagenin acetate. / Pettit, George; Kasturi, T. R.

In: Journal of Organic Chemistry, Vol. 26, No. 11, 1961, p. 4553-4556.

Research output: Contribution to journalArticle

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