Steroidal δ-Alkenyl Oximes as Ambident Nucleophiles: Electrophile- Induced Formation of Oxazepane Derivatives in the Bis-Estrone Series

Author(s): Janos Wolfling, Erzsebet Mernyak, Zsolt Bikadi, Eszter Hazai, Laszlo Mark, Gyula Schneider.

Journal Name:Letters in Organic Chemistry

Volume 5 , Issue 1 , 2008

Abstract:

Electrophile-induced cyclization of steroidal δ-alkenyl oximes and oxime ethers and subsequent hydride reduction of the cyclic nitrones led to new halogenated or selenylated N-hydroxy- or N-benzyloxy-aza-D-homo-estrones. Starting from a 13β-D-secoestrone oxime or oxime ether, steroidal dimers were isolated in intermolecular 1,3-dipolar cycloaddition of the cyclic nitrone to the C=N double bond of the oxazepine intermediates.

Keywords: Selenium, oxazepane, 1,3-dipolar cycloadditions, stereoselectivity, dimeric steroids, estrone derivatives

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Article Details

VOLUME: 5
ISSUE: 1
Year: 2008
Page: [17 - 21]
Pages: 5
DOI: 10.2174/157017808783330243

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