Efficient microwave assisted access to chiral O-(alpha-protected-aminoacyl)steroids.
Chiral O-(alpha-protected-aminoacyl)steroids 4a-f, 6a-b, 8 and 4a+4d and O-(alpha-protected-dipeptidoyl)steroids 12a,b are conveniently prepared under microwave irradiation in isolated yields of 65-96%, with complete chirality retention. The reaction utilized readily available N-(Z-alpha-aminoacyl)benzotriazoles 2a-f and Z-dipeptidoylbenzotriazole 11, with naturally occurring steroidal alcohols 3,5,7,9.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, 32611-7200, USA. katritzky@chem.ufl.edu
Angrish
Parul
P
D052160:Benzothiazoles / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D004526:Efficiency / Q000528:radiation effects*; D004951:Esterification / Q000528:radiation effects*; D009682:Magnetic Resonance Spectroscopy; D008872:Microwaves; D008954:Models, Biological; D008968:Molecular Conformation; D010636:Phenols / Q000737:chemistry; D011827:Radiation; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry
D052160:Benzothiazoles; D010636:Phenols; D013256:Steroids