Diels-Alder reaction of androsta-14,16-dien-17-yl acetates with nitroethylene: product distribution and selected adduct transformations

Alexander V Baranovsky; Dmitry A Bolibrukh; Vladimir A Khripach; Bernd Schneider

doi:10.1016/j.steroids.2012.11.015

Diels-Alder reaction of androsta-14,16-dien-17-yl acetates with nitroethylene: product distribution and selected adduct transformations

Steroids. 2013 Feb;78(2):282-7. doi: 10.1016/j.steroids.2012.11.015. Epub 2012 Dec 19.

Authors

Alexander V Baranovsky¹, Dmitry A Bolibrukh, Vladimir A Khripach, Bernd Schneider

Affiliation

¹ Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Minsk, Belarus. [email protected]

PMID: 23261956
DOI: 10.1016/j.steroids.2012.11.015

Abstract

The Diels-Alder cycloaddition of nitroethylene to some androsta-14,16-dien-17-yl acetates has been studied. The addition occurs stereoselectively, giving predominantly head-to-head-adduct. 14β-Cyanomethyl steroids were obtained via the reductive cleavage reaction of bridged nitro compounds. The structures of the new compounds have been fully characterized by 2D NMR and tandem mass-spectrometry methods.

MeSH terms

Androstanes / chemistry*
Cycloaddition Reaction*
Ethylenes / chemistry*
Indicators and Reagents
Magnetic Resonance Spectroscopy

Substances

Androstanes
Ethylenes
Indicators and Reagents
ethylene