Michael Tolar Martin

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

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.

Practical acid-catalyzed acylation of sulfonamides with carboxylic acid anhydrides

A highly efficient reaction between sterically and electronically diverse sulfonamides and carboxylic acid anhydrides to furnish monoacylated N-acylsulfonamides is described. This represents the first systematic disclosure of the scope of sulfuric acid-catalyzed acylation of sulfonamides.

Direct synthesis of thioethers from sulfonyl chlorides and activated alcohols

An efficient, safe one-pot synthesis of thioethers from aromatic sulfonyl chlorides and activated alcohols has been developed under non-aqueous conditions.