Xiao-Xin Shi

A short and practical synthesis of oseltamivir phosphate (Tamiflu) from (-)-shikimic acid.

Oseltamivir phosphate (1) was synthesized from (-)-shikimic acid through a short and practical synthetic route via eight steps in 47% overall yield. In addition, the highly regioselective and stereoselective nucleophilic replacement of OMs by the N(3) group in the third and seventh steps has been studied in detail, and the reaction conditions were optimized.

Mild and Efficient Syntheses of 1-Aryl-3,4-dihydroisoquinolines and 1-Aryl-3,4-dihydro-β-carbolines via Regiospecific β-Eliminations of the Corresponding N-Tosyl-1,2,3,4-tetrahydroisoquinolines and N-Tosyl-1,2,3,4-tetrahydro-β-carbolines

Abstract Treatment of N-tosyl-1-aryl-1,2,3,4-tetrahydro-isoquinolines or N-tosyl-1-aryl-1,2,3,4-tetrahydro-β-carbolines with a strong base such as NaOH or KOH at 70 °C in dimethylsulfoxide (DMSO) produced 1-aryl-3,4-dihydroisoquinolines or 1-aryl-3,4-dihydro-β-carbolines in good yields via mild and regiospecific β-eliminations. A dramatic solvent effect was observed, DMSO was crucial for the reactions. The temperature is also crucial for the reactions and should be kept between 60 and 80 °C. GRAPHICAL ABSTRACT

Synthesis of Diaryl Disulfides via Mild Reduction of Arylsulfinates with Hydrazine Monohydrate in DMSO

Abstract Arylsulfinates were reduced with hydrazine monohydrate at room temperature in dimethylsulfoxide (DMSO) to afford diaryl disulfides in good yields. A dramatic solvent effect was observed, and DMSO was found to be the best solvent for the reaction. GRAPHICAL ABSTRACT

Asymmetric syntheses of both enantiomers of amphetamine hydrochloride via bakers‘ yeast reduction of phenylacetone

Both enantiomers of amphetamine hydrochloride were stereospecifically synthesised based on bakers’ yeast reduction of phenylacetone. A simple and efficient method for the chiral inversion of (S)-1-phenyl-2-propanol 3 to (R)-1-phenyl-2-propanol 8 has been discussed.