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Synlett 1991; 1991(11): 841-844
DOI: 10.1055/s-1991-20898
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Synthesis and Reactions of a Homochiral Hydroxythiol Derived from Tartaric Acid

Ottorino De Lucchi* , Paola Maglioli, Giovanna Delogu, Giovanni Valle
  • *Dipartimento di Chimica, Università di Sassari, via Vienna 2, I-07100 Sassari, Italy
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Publication Date:
07 March 2002 (online)

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The synthesis of the homochiral, crystalline hydroxythiol 1 (2,3-isopropylidenedioxy-4-mercapto-1,1,4,4-tetraphenyl-1-butanol) from tartaric acid is described. Compound 1 gives with dibromomethane the oxathiepane 3 (5,6-isopropylidenedioxy-4,4,7,7-tetraphenyl-1,3-oxathiepane) which reacts with butyllithium and methyl iodide to afford the 2,2-dimethylated product 7. The lithium derivative of 3 rearranges at temperatures higher than -50 °C to the thiol 8 (3,4-isopropylidenedioxy-6-mercapto-2,2,5, 5-tetraphenyltetrahydropyran). The structures of 7 and 8 were ascertained by X-ray diffraction. The 1,3-oxathiepane 3 was oxidized with total stereoselectively to the single sulfoxide 10. S-methylation of 1 gave 12 which was diastereoselectively oxidized to a single sulfoxide 13.