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

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

doi:10.1016/j.steroids.2012.11.015

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

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Schneider, Bernd
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;

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Citation

Baranovsky, A. V., Bolibrukh, D. A., Khripach, V. A., & Schneider, B. (2012). Diels–Alder reaction of androsta-14,16-dien-17-yl acetates with nitroethylene: Product distribution and selected adduct transformations. Steroids, 78, 282-287. doi:10.1016/j.steroids.2012.11.015.

Cite as: https://hdl.handle.net/11858/00-001M-0000-000E-70C8-1

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.