Microbial transformations of terpenoids with 1-p-menthene skeleton

Monoterpenoids with 1-p-menthene-structure can be transformed by Corynespora cassiicola DSM 62 474, DSM 62 475, and Diplodia gossypina ATCC 10 936 to chiral 1,2-trans-diols in yields of more than 60% with only minor amounts of side-products. Whereas the substrates (S)-(-)-limonene, a-terpinene, ?-terpinene, and terpinolene are converted to the (1R,2R)-p-menthene-1,2-diols, (R)-(+)-limonene and (R)-(-)-phellandrene yield the (1S,2S)-1,2-diols. For the transformation of (S)-a-terpineol and (S)-a-terpinene-4-ol to the (1S,2S)-1,2-diols Gibberella cyanea DSM 62 719 can be used, which however oxidizes parallel at the 6- and 7-position.