Abstract
Synthesis of ( S)-3-mercapto-1-heptyl acetate was achieved in four steps. Sharpless asymmetric epoxidation of ( E)-2-heptenol yielded (2 R,3 R)-2,3-epoxy-1-heptanol, which was treated with thiourea in the presence of Ti(OPri)4 to give (2 S,3 S)-2,3-epithio-1-heptanol, reduction of which followed by acetylation afforded ( S)-3-mercapto-1-heptyl acetate in 91% ee. The optically active product possessed a tropical fruit aroma reminiscent of mango and passion fruit, with berry, ester-like, sweet, and pepper-like aspects.
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