PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids
Reaction of 11-pregnene-3,20-dione (6) or 3-α-acetoxy-11-pregnen-20-one (12) with trimethylsilylethanesulfonyl ('Ses') iminoiodinane 5 in the presence of copper (I) triflate gave the corresponding α,α-11,12-aziridino steroids 7 and 13 in 53 and 45% yields, respectively. The Ses group of ea...
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2003
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paper:paper_00404020_v59_n7_p1009_DiChenna2023-06-08T15:04:16Z PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids Di Chenna, Pablo Héctor Ghini, Alberto Antonio Burton, Gerardo Aziridine Iminoiodinane Ses group Steroid 3alpha acetoxy 5beta h 11 pregnen 20 one 3alpha acetoxy n [2 (trimethylsilyl)ethanesulfonyl] 11alpha,12alpha aziridino 5beta h pregnan 20 one 3alpha hydroxy n methyl 11alpha,12alpha aziridino 5beta h pregnan 20 one alkane derivative aziridine derivative copper derivative eltanolone iodine derivative ketone derivative n [2 (trimethylsilyl)ethanesulfonyl] 11alpha,12alpha aziridino 5beta h pregnane 3,20 dione n methyl 11alpha,12alpha aziridino 5beta h pregnane 3,20 dione neurosteroid pregnane derivative trimethylsilyl derivative unclassified drug article aziridination catalysis chemical reaction drug conformation drug synthesis methylation priority journal proton nuclear magnetic resonance stereochemistry X ray crystallography Reaction of 11-pregnene-3,20-dione (6) or 3-α-acetoxy-11-pregnen-20-one (12) with trimethylsilylethanesulfonyl ('Ses') iminoiodinane 5 in the presence of copper (I) triflate gave the corresponding α,α-11,12-aziridino steroids 7 and 13 in 53 and 45% yields, respectively. The Ses group of each compound was removed using the TASF reagent and the resulting free aziridine NH was methylated to afford the 11α,12α-N-methyl aziridinosteroids 9 and 15, respectively. The latter is a conformationally constrained analogue of the endogenous neurosteroid pregnanolone (1). © 2003 Elsevier Science Ltd. All rights reserved. Fil:Di Chenna, P.H. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ghini, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2003 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v59_n7_p1009_DiChenna http://hdl.handle.net/20.500.12110/paper_00404020_v59_n7_p1009_DiChenna |
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Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Aziridine Iminoiodinane Ses group Steroid 3alpha acetoxy 5beta h 11 pregnen 20 one 3alpha acetoxy n [2 (trimethylsilyl)ethanesulfonyl] 11alpha,12alpha aziridino 5beta h pregnan 20 one 3alpha hydroxy n methyl 11alpha,12alpha aziridino 5beta h pregnan 20 one alkane derivative aziridine derivative copper derivative eltanolone iodine derivative ketone derivative n [2 (trimethylsilyl)ethanesulfonyl] 11alpha,12alpha aziridino 5beta h pregnane 3,20 dione n methyl 11alpha,12alpha aziridino 5beta h pregnane 3,20 dione neurosteroid pregnane derivative trimethylsilyl derivative unclassified drug article aziridination catalysis chemical reaction drug conformation drug synthesis methylation priority journal proton nuclear magnetic resonance stereochemistry X ray crystallography |
| spellingShingle |
Aziridine Iminoiodinane Ses group Steroid 3alpha acetoxy 5beta h 11 pregnen 20 one 3alpha acetoxy n [2 (trimethylsilyl)ethanesulfonyl] 11alpha,12alpha aziridino 5beta h pregnan 20 one 3alpha hydroxy n methyl 11alpha,12alpha aziridino 5beta h pregnan 20 one alkane derivative aziridine derivative copper derivative eltanolone iodine derivative ketone derivative n [2 (trimethylsilyl)ethanesulfonyl] 11alpha,12alpha aziridino 5beta h pregnane 3,20 dione n methyl 11alpha,12alpha aziridino 5beta h pregnane 3,20 dione neurosteroid pregnane derivative trimethylsilyl derivative unclassified drug article aziridination catalysis chemical reaction drug conformation drug synthesis methylation priority journal proton nuclear magnetic resonance stereochemistry X ray crystallography Di Chenna, Pablo Héctor Ghini, Alberto Antonio Burton, Gerardo PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids |
| topic_facet |
Aziridine Iminoiodinane Ses group Steroid 3alpha acetoxy 5beta h 11 pregnen 20 one 3alpha acetoxy n [2 (trimethylsilyl)ethanesulfonyl] 11alpha,12alpha aziridino 5beta h pregnan 20 one 3alpha hydroxy n methyl 11alpha,12alpha aziridino 5beta h pregnan 20 one alkane derivative aziridine derivative copper derivative eltanolone iodine derivative ketone derivative n [2 (trimethylsilyl)ethanesulfonyl] 11alpha,12alpha aziridino 5beta h pregnane 3,20 dione n methyl 11alpha,12alpha aziridino 5beta h pregnane 3,20 dione neurosteroid pregnane derivative trimethylsilyl derivative unclassified drug article aziridination catalysis chemical reaction drug conformation drug synthesis methylation priority journal proton nuclear magnetic resonance stereochemistry X ray crystallography |
| description |
Reaction of 11-pregnene-3,20-dione (6) or 3-α-acetoxy-11-pregnen-20-one (12) with trimethylsilylethanesulfonyl ('Ses') iminoiodinane 5 in the presence of copper (I) triflate gave the corresponding α,α-11,12-aziridino steroids 7 and 13 in 53 and 45% yields, respectively. The Ses group of each compound was removed using the TASF reagent and the resulting free aziridine NH was methylated to afford the 11α,12α-N-methyl aziridinosteroids 9 and 15, respectively. The latter is a conformationally constrained analogue of the endogenous neurosteroid pregnanolone (1). © 2003 Elsevier Science Ltd. All rights reserved. |
| author |
Di Chenna, Pablo Héctor Ghini, Alberto Antonio Burton, Gerardo |
| author_facet |
Di Chenna, Pablo Héctor Ghini, Alberto Antonio Burton, Gerardo |
| author_sort |
Di Chenna, Pablo Héctor |
| title |
PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids |
| title_short |
PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids |
| title_full |
PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids |
| title_fullStr |
PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids |
| title_full_unstemmed |
PhI=NSes mediated aziridination of 11-pregnane derivatives: Synthesis of an 11,12-aziridino analogue of neuroactive steroids |
| title_sort |
phi=nses mediated aziridination of 11-pregnane derivatives: synthesis of an 11,12-aziridino analogue of neuroactive steroids |
| publishDate |
2003 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v59_n7_p1009_DiChenna http://hdl.handle.net/20.500.12110/paper_00404020_v59_n7_p1009_DiChenna |
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