The stereochemistry of the Grignard reaction of steroidal 4,5-epoxy-3-ketones

Cavit Uyanik; Aslihan Malay; Azra S Ayna; James R Hanson; Peter B Hitchcock

doi:10.1016/j.steroids.2004.09.002

The stereochemistry of the Grignard reaction of steroidal 4,5-epoxy-3-ketones

Steroids. 2005 Feb;70(2):71-5. doi: 10.1016/j.steroids.2004.09.002. Epub 2004 Dec 22.

Authors

Cavit Uyanik¹, Aslihan Malay, Azra S Ayna, James R Hanson, Peter B Hitchcock

Affiliation

¹ Department of Chemistry, Kocaeli University, Izmit 41300, Kocaeli, Turkey. cuyanik@kou.edu.tr

PMID: 15631862
DOI: 10.1016/j.steroids.2004.09.002

Abstract

The stereochemistry of the addition of methylmagnesium bromide to a steroidal 4,5-epoxy-3-ketone has been shown to be determined by the stereochemistry of the epoxide. The epoxidation to the corresponding 3-alkyl-3-hydroxy-4-enes by per-acid was determined by the stereochemistry of the allylic alcohol.

MeSH terms

Bromides / chemistry
Crystallography, X-Ray
Indicators and Reagents / chemistry
Ketones / chemical synthesis*
Ketones / chemistry
Magnesium / chemistry
Models, Molecular
Organometallic Compounds / chemistry*
Stereoisomerism
Steroids / chemical synthesis*
Steroids / chemistry

Substances

Bromides
Indicators and Reagents
Ketones
Organometallic Compounds
Steroids
Magnesium