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J Org Chem. 2001 Apr 20;66(8):2700-4.

Novel sparteine-mediated enantio-dichotomic formal synthesis of R-(-)- and S-(+)-curcuphenol.

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  • 1Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku 606-8501, Kyoto, Japan.


High and opposite enantiodiscriminations were observed between tertiary amides and secondary amides in the sparteine-mediated lateral metalation-allylation of 2-ethyl-m-toluamide derivatives (2a, 2e). The results described above have been applied for the formal synthesis of both enantiomers of curcuphenol. The brief mechanistic studies suggested that stereoinformation was introduced after the deprotonation step.

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