Conjugate hydrocyanation of 17-acetyl-11-carbomethoxygona-1,3,5(10),13(17)-tetraenes.
The conjugate hydrocyanation of 17-acetylgona-11-carbomethoxy-1,3,5(10),13(17)-tetraenes using diethylaluminum cyanide (Nagata reaction) is reported. This methodology has allowed the introduction of an angular cyano group at the C-13 position of the steroid skeleton. Subsequent reduction of the nitrile group yielded various functionalized steroids. One of them, 22 bears the natural trans/anti/trans stereochemistry and possesses an hydroxyl and aminomethyl functionalities in the positions 11beta and 13beta, respectively. The characteristic (1)H and (13)C NMR spectroscopic features of the synthesized steroids are reported.
Pellissier
Hélène
H
UMR 6180 CNRS and Université d'Aix Marseille III: Chirotechnologies: catalyse et biocatalyse, Laboratoire de Synthèse Organique associé au CNRS, Avenue Escadrille Normandie Niémen, 13397 Marseille Cedex 20, France.
Michellys
Pierre-Yves
PY
Santelli
Maurice
M
D000107:Acetylation; D003485:Cyanates / Q000737:chemistry*; D006067:Gonanes / Q000737:chemistry*; D006856:Hydrogen Cyanide / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008968:Molecular Conformation; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry*; D013329:Structure-Activity Relationship
D003485:Cyanates; D006067:Gonanes; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D013256:Steroids; C488013:diethylaluminum cyanide; D006856:Hydrogen Cyanide