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

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

Volume: 5 Issue: 1

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

Affiliation:

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

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.

Cite this article as:

Wolfling Janos, Mernyak Erzsebet, Bikadi Zsolt, Hazai Eszter, Mark Laszlo and Schneider Gyula, Steroidal δ-Alkenyl Oximes as Ambident Nucleophiles: Electrophile- Induced Formation of Oxazepane Derivatives in the Bis-Estrone Series, Letters in Organic Chemistry 2008; 5 (1) . https://dx.doi.org/10.2174/157017808783330243