Aluminum Chloride-Catalyzed Opening of the Steroidal Sapogenin Spiroketal System

George R. Pettit; William J. Bowyer

doi:10.1021/jo01071a023

Aluminum Chloride-Catalyzed Opening of the Steroidal Sapogenin Spiroketal System

George R. Pettit, William J. Bowyer

Research output: Contribution to journal › Article › peer-review

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Abstract

Several representative steroidal sapogenins have been conveniently converted to the corresponding dihydrosapogenins employing the lithium aluminum hydride-aluminum chloride reagent. Dihydro derivatives of lla-hydroxytigogenin, marko-genin, and three previously described dihydrosapogenins were prepared by the new procedure. Lithium aluminum hydride reduction of tomatidine, in the presence of aluminum chloride, provided both isomers of dihydrotomatidine.

Original language	English (US)
Pages (from-to)	84-86
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	25
Issue number	1
DOIs	https://doi.org/10.1021/jo01071a023
State	Published - Jan 1 1960
Externally published	Yes

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Organic Chemistry

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10.1021/jo01071a023

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title = "Aluminum Chloride-Catalyzed Opening of the Steroidal Sapogenin Spiroketal System",

abstract = "Several representative steroidal sapogenins have been conveniently converted to the corresponding dihydrosapogenins employing the lithium aluminum hydride-aluminum chloride reagent. Dihydro derivatives of lla-hydroxytigogenin, marko-genin, and three previously described dihydrosapogenins were prepared by the new procedure. Lithium aluminum hydride reduction of tomatidine, in the presence of aluminum chloride, provided both isomers of dihydrotomatidine.",

author = "Pettit, {George R.} and Bowyer, {William J.}",

year = "1960",

month = jan,

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doi = "10.1021/jo01071a023",

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AU - Pettit, George R.

AU - Bowyer, William J.

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Y1 - 1960/1/1

N2 - Several representative steroidal sapogenins have been conveniently converted to the corresponding dihydrosapogenins employing the lithium aluminum hydride-aluminum chloride reagent. Dihydro derivatives of lla-hydroxytigogenin, marko-genin, and three previously described dihydrosapogenins were prepared by the new procedure. Lithium aluminum hydride reduction of tomatidine, in the presence of aluminum chloride, provided both isomers of dihydrotomatidine.

AB - Several representative steroidal sapogenins have been conveniently converted to the corresponding dihydrosapogenins employing the lithium aluminum hydride-aluminum chloride reagent. Dihydro derivatives of lla-hydroxytigogenin, marko-genin, and three previously described dihydrosapogenins were prepared by the new procedure. Lithium aluminum hydride reduction of tomatidine, in the presence of aluminum chloride, provided both isomers of dihydrotomatidine.

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Aluminum Chloride-Catalyzed Opening of the Steroidal Sapogenin Spiroketal System

Abstract

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