Carvone Pseudomonas ovalis

A Pseudomonas strain hydroxylates p-menthane to cis-p-menthan-l-ol,84 and microbiological reduction of carvotanacetone with Pseudomonas ovalis gives similar results85 to those obtained with carvone (Vol. 5, p. 24, incorrectly reports inversion at C-4). (—)-Carvotanacetone (30) gives (+)-carvomenthone (31), (—)-... 

Both naturally occurring enantiomers of carvone were selectively reduced by B. sulfurescens (Scheme 71). (-)-Carvone was reduced to (-h)-dihydrocarvone (trans) and further to (-H)-neodihydrocarveol, whereas (-i-)-carvone was reduced to (-)-isodihydrocarvone (cis), which was then converted to (-)-neo-isodihydrocarveol. Similar reductions with identical stereoselectivities were observed earlier with Pseudomonas ovalis (strain 6-1) and with a strain of Aspergillus niger. ... 

FIGURE 19.108 Metabolic pathways of (+)-carvone (93) by Pseudomonas ovalis strain 6-1 and other many microorganisms. (Modi ed from Noma. Y. et al., Agric. Biol. Chem., 38, 735,1974b.)... 

Noma, Y., 1977. Conversion of the analogues of carvone and dihydrocarvone by Pseudomonas ovalis, strain 6-1, Biochemical reduction of terpenes, part VII. 463-470. 

Noma, Y., S. Nonomura, H. Ueda, and C. Tatsumi, 1974c. Conversion of (+)-carvone by Pseudomonas ovalis, strain 6-1(1).38 735-740. 

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