Stereochemistry of microbiological hydroxylations of 1, 4-cineole

…, A Goswami, RP Steffek, RL Chapman…

Index: Liu, Wei-Guo; Goswami, Animesh; Steffek, Robin Paulson; Chapman, Robert L.; Sariaslani, F. Sima; et al. Journal of Organic Chemistry, 1988 , vol. 53, # 24 p. 5700 - 5704

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Citation Number: 26

Abstract

The stereochemistries of microbial hydroxylations of l-methyl-4-(l-methylethyl)-7-oxabicyclo [2.2. 1] heptane (1, 4-cineole) were examined with Bacillus cereus and Streptomyces griseus as biocatalysts. Growing cultures of these bacteria introduce hydroxyl groups primarily at the 2-and 8-positions of the monoterpene substrate. Hydroxylation at position 2 destroys the C, symmetry of 1, 4-cineole and allows the possibility of creating two pairs of ...