Steroidal δ-alkenyl oximes as ambident nucleophiles: Electrophile-induced formation of oxazepane derivatives in the bis-estrone series

E. Mernyák, Zsolt Bikádi, Eszter Hazai, L. Márk, G. Schneider, J. Wölfling

Research output: Contribution to journalArticle

10 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)17-21
Number of pages5
JournalLetters in Organic Chemistry
Volume5
Issue number1
DOIs
Publication statusPublished - Jan 2008

Fingerprint

Nucleophiles
Oximes
Estrone
Derivatives
Oxazepines
Ethers
Cycloaddition
Cyclization
Cycloaddition Reaction
Hydrides
Dimers
Ether
nitrones

Keywords

  • 1,3-dipolar cycloadditions
  • Dimeric steroids
  • Estrone derivatives
  • Oxazepane
  • Selenium
  • Stereoselectivity

ASJC Scopus subject areas

  • Organic Chemistry
  • Biochemistry

Cite this

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T2 - Electrophile-induced formation of oxazepane derivatives in the bis-estrone series

AU - Mernyák, E.

AU - Bikádi, Zsolt

AU - Hazai, Eszter

AU - Márk, L.

AU - Schneider, G.

AU - Wölfling, J.

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AB - 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.

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KW - Dimeric steroids

KW - Estrone derivatives

KW - Oxazepane

KW - Selenium

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