Chemical and microbiological remote functionalisation of (+)-and (-)-bornyl acetate

MS Allen, N Darby, P Salisbury…

Index: Allen; Darby; Salisbury; et al. Canadian Journal of Chemistry, 1979 , vol. 57, # 7 p. 733 - 741

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Citation Number: 32

Abstract

Chemical oxidation of (-)-bornyl acetate provides a mixture of 3-, 5-, and 6-oxobornyl acetate, whereas microbiological hydroxylation with cultures of Helminthosporium sativum gives a mixture of 2, 3-, 2, 6-, and 2, 5-bornanediols. In each case the reaction occurs preferentially at the C (5) position. Microbiological hydroxylation of (+)-bornyl acetate with H. sativum occurs almost exclusively at the C (5) position. Regiospecific hydroxylation of (+)- ...