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

George R. Pettit; T. R. Kasturi

doi:10.1021/jo01069a086

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

George R. Pettit, T. R. Kasturi

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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 language	English (US)
Pages (from-to)	4553-4556
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	26
Issue number	11
DOIs	https://doi.org/10.1021/jo01069a086
State	Published - Nov 1961
Externally published	Yes

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Organic Chemistry

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

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.",

author = "Pettit, {George R.} and Kasturi, {T. R.}",

year = "1961",

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T1 - Steroids and Related Natural Products. VII. Boron Trifluoride Etherate-Lithium Aluminum Hydride Reduction of Smilagenin Acetate

AU - Pettit, George R.

AU - Kasturi, T. R.

PY - 1961/11

Y1 - 1961/11

N2 - 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.

AB - 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.

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

Abstract

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