| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1349274 | Tetrahedron: Asymmetry | 2006 | 10 Pages |
Reversing the polarity of the cycloaddition partners in Dane’s steroid synthesis provides ready access to enantiomerically pure, functionally-rich steroidal structures.
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N-(1S)-[(2R,3R)-6-Benzyloxy-3-hydroxy-2-allyl-hex-4-ynoyl]-bornane-10,2-sultamC26H33NO5SEe, de >95% (NMR)[α]D = −52.0 (c 0.50, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,3R)
N-(1S)-[(2R)-2-((1R)-1-Hydroxy-3-phenyl-2-propyn-1-yl)-4-pentenoyl]bornane-10,2-sultamC24H29NO4SEe, de >95% (NMR)[α]D21=-91.0 (c 0.73, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,1R)
N-(1S)-[(2R)-2-((1R)-1-Hydroxy-3-trimethylsilyl-2-propyn-1-yl)-4-pentenoyl]bornane-10,2-sultamC21H33NO4SSiEe, de >95% (NMR)[α]D20=-90.0 (c 0.95, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,1R)
N-(1S)-[1-[(1R,2R)-2-Hydroxy-3-(3-(benzyloxy)prop-1-en-2-yl)-3-cyclopentenyl]carbonyl]bornane-10,2-sultamC26H33NO5SEe, de >95% (NMR)[α]D = −29.2 (c 0.25, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2R)
N-(1S)-[1-[(1R,2R)-2-Hydroxy-3-(1-phenylethen-1-yl)-3-cyclopentenyl]carbonyl]bornane-10,2-sultamC24H29NO4SEe, de >95% (NMR)[α]D21=-24 (c 0.70, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration:(1R,2R)
N-(1S)-[1-[(1R,2R)-2-Hydroxy-3-(1-trimethylsilylethen-1-yl)-3-cyclopentenyl]carbonyl]bornane-10,2-sultamC21H33NO4SSiEe, de >95% (NMR)[α]D20=-34.5 (c 0.48, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2R)
N-(1S)-[1-[(1S,2R)-2-Hydroxy-3-(1-trimethylsilylethen-1-yl)-3-cyclopentenyl]carbonyl]bornane-10,2-sultamC21H33NO4SSiEe, de >95% (NMR)[α]D = −72.9 (c 1.1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,2R)
N-(1S)-[(2R,3R)-6-Benzyloxy-3-triethylsilyloxy-2-propen-3-yl-hex-4-ynoyl]bornane-10,2-sultamC32H47NO5SSiEe, de >95% (NMR)[α]D = −27.2 (c 1.04, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,3R)
N-(1S)-[1-[(1R,2R)-2-Triethylsilyloxy-3-(3-(benzyloxy)prop-1-en-2-yl)-3-cyclopentenyl]carbonyl]bornane-10,2-sultamC32H47NO5SSiEe, de >95% (NMR)[α]D = +18.1 (c 0.30, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2R)
N-(1S)-[1-[(1R,2R)-2-Triethylsilyloxy-3-(1-phenylethen-1-yl)-3-cyclopentenyl]carbonyl]bornane-10,2-sultamC30H43NO4SSiEe, de >95% (NMR)[α]D22=+58 (c 1.0, chloroform)Source of chirality:asymmetric synthesisAbsolute configuration: (1R,2R)
N-(1S)-[16-[(8R,9R,14R,16R,17R)-12-(Benzyloxymethyl)-17-hydroxy-8-nitro-6,7-dioxo-7,8,9,11,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene]carbonyl]bornane-10,2-sultamC36H38N2O9SEe, de >95% (NMR)[α]D = +9.5 (c 0.15, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (8R,9R,14R,16R,17R)
N-(1S)-[16-(8R,9R,14R,16R,17R)-12-(Benzyloxymethyl)-8-nitro-6,7-dioxo-17-(triethylsilyloxy)-7,8,9,11,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene]carbonyl]bornane-10,2-sultamC42H52N2O9SSiEe, de >95% (NMR)[α]D = +30.1 (c 1.0, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (8R,9R,14R,16R,17R)
N-(1S)-[16-[(8R,9R,14R,16R,17R)-8-Nitro-6,7-dioxo-12-phenyl-17-triethylsilyloxy-7,8,9,11,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene]carbonyl]bornane-10,2-sultamC40H48N2O8SSiEe, de >95% (NMR)[α]D22=+51 (c 1.0, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (8R,9R,14R,16R,17R)
N-(1S)-[2-[(2R,3R,5aS,11aR,11bS)-4-(Benzyloxymethyl)-3-hydroxy-6,11-dioxo-2,3,5,5a,6,11,11a,11b-octahydro-1H-cyclopenta[a]anthracene]carbonyl]bornane-10,2-sultamC36H39NO7SEe, de >95% (NMR)[α]D = +12.5 (c 0.30, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,3R,5aS,11aR,11bS)
N-(1S)-[2-[(2R,3R,5aS,11aR,11bS)-3-Hydroxy-6,11-dioxo-4-phenyl-2,3,5,5a,6,11,11a,11b-octahydro-1H- cyclopenta[a]anthracene]carbonyl]bornane-10,2-sultamC34H35NO6SEe, de >95% (NMR)[α]D21=-21.2 (c 0.58, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,3R,5aS,11aR,11bS)
N-(1S)-[2-[(2R,3R,5aS,11aR,11bS)-3-Hydroxy-6,11-dioxo-4-trimethylsilyl-2,3,5,5a,6,11,11a,11b-octahydro-1H-cyclopenta[a]anthracene]carbonyl]bornane-10,2-sultamC31H39NO6SSiEe, de >95% (NMR)[α]D21=+37 (c 0.80, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,3R,5aS,11aR,11bS)
N-(1S)-[2-[(2R,3R,5aS,11aR,11bS)-4-(Benzyloxymethyl)-3-triethylsilyloxy-6,11-dioxo-2,3,5,5a,6,11,11a,11b-octahydro-1H-cyclopenta[a]anthracene]carbonyl]bornane-10,2-sultamC42H53NO7SSiEe, de >95% (NMR)[α]D = +5.1 (c 0.40, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,3R,5aS,11aR,11bS)
N-(1S)-[2-[(2R,3R,5aS,11aR,11bS)-3-Triethylsilyloxy-6,11-dioxo-4-phenyl-2,3,5,5a,6,11,11a,11b-octahydro-1H-cyclopenta[a]anthracene]carbonyl]bornane-10,2-sultamC34H34NO5SEe, de >95% (NMR)[α]D21=+38.4 (c 1.1, chloroform)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,3R,5aS,11aR,11bS)
