An efficient, scalable synthesis of the HIV reverse transcriptase inhibitor Ziagen®(1592U89)

…, MT Martin, BR Sickles, DA Livingston

Index: Daluge, Susan M.; Martin, Michael T.; Sickles, Barry R.; Livingston, Douglas A. Nucleosides, Nucleotides and Nucleic Acids, 2000 , vol. 19, # 1-2 p. 297 - 327

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Citation Number: 79

Abstract

Abstract Ziagen®,(1S, cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene- 1-methanol, was synthesized from (1S, 4R)-azabicyclo [2.2. 1] hept-5-en-3-one by efficient processes which bypass problematic steps in earlier routes. 2-Amino-4, 6-dichloro-5- formamidopyrimidine is a key intermediate which makes possible an efficient construction of the purine from a chiral cyclopentenyl precursor.