Copper-Catalyzed Cyclization of Steroidal Acylaminoacetylenes:  Syntheses of Novel 11β-Aryl-17,17- spiro[(4‘H,5‘-methylene)oxazol]-Substituted Steroids

Copper-Catalyzed Cyclization of Steroidal Acylaminoacetylenes:  Syntheses of Novel 11β-Aryl-17,17- spiro[(4‘H,5‘-methylene)oxazol]-Substituted Steroids

A variety of novel 11β-aryl-17,17-spiro[(4‘H,5‘-methylene)oxazol]-substituted steroids have been synthesized in moderate to good yields via copper-catalyzed cyclization of acylaminoacetylenes. The best result was obtained with a catalytic amount of CuI in 1:1 benzene−Et3N at 90 °C for 30 min (Ar = 3...

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Veröffentlicht in:Organic letters 2007-05, Vol.9 (10), p.1887-1890
Hauptverfasser: Jin, Chunyang, Burgess, Jason P, Kepler, John A, Cook, C. Edgar
Format: Artikel
Sprache:eng
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Zusammenfassung:A variety of novel 11β-aryl-17,17-spiro[(4‘H,5‘-methylene)oxazol]-substituted steroids have been synthesized in moderate to good yields via copper-catalyzed cyclization of acylaminoacetylenes. The best result was obtained with a catalytic amount of CuI in 1:1 benzene−Et3N at 90 °C for 30 min (Ar = 3,4-difluorophenyl; R = ethyl; 97% yield).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol070447d