Microbial transformations. 12. Regiospecific and asymmetric oxidation of the remote double bond of geraniol

JD Fourneron, A Archelas…

Index: Fourneron, J. D.; Archelas, A.; Furstoss, R. Journal of Organic Chemistry, 1989 , vol. 54, # 19 p. 4686 - 4689

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Citation Number: 51

Abstract

Results When submitted to a 36-h culture of Aspergillus niger, geranyl N-phenylcarbamate (1) was metabolized to diol 3, which was isolated by direct crystallization from the crude extract (49% yield)(Scheme I). Its structure was unambiguously established by conventional'H NMR analysis. The enantiomeric excess of this diol was determined by analysis of its (-)-camphanyl derivative: which indicated an ee> 95%. 1