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

39 Scopus citations

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 - 1960
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo01071a023

Cite this

@article{b6d822523d5d49be826a1aee89ae728e,

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",

doi = "10.1021/jo01071a023",

language = "English (US)",

volume = "25",

pages = "84--86",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Aluminum Chloride-Catalyzed Opening of the Steroidal Sapogenin Spiroketal System

AU - Pettit, George R.

AU - Bowyer, William J.

PY - 1960

Y1 - 1960

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.

UR - http://www.scopus.com/inward/record.url?scp=0002270733&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0002270733&partnerID=8YFLogxK

U2 - 10.1021/jo01071a023

DO - 10.1021/jo01071a023

M3 - Article

AN - SCOPUS:0002270733

SN - 0022-3263

VL - 25

SP - 84

EP - 86

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 1

ER -

Aluminum Chloride-Catalyzed Opening of the Steroidal Sapogenin Spiroketal System

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this