Synthesis of carbovir and abacavir from a carbocyclic precursor.
A facile method for the synthesis of a carbocyclic analog of 2',3'-didehydro-2',3'-dideoxy-2-amino-6-chloropurine is presented, starting from the versatile lactam, 2-azabicyclo[2.2.1]hept-5-en-3-one. The corresponding anti-HIV nucleoside analogs, carbovir and its derivative abacavir, are prepared directly from the 6-chloro intermediate in one-step reactions.
Vince
Robert
R
Center for Drug Design, University of Minnesota, Minneapolis, Minnesota, USA.
Hua
Mei
M
D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D000099227:Abacavir
D015224:Dideoxynucleosides; D018894:Reverse Transcriptase Inhibitors; D000099227:Abacavir; C057503:carbovir