MICROBIAL OXIDATION IN SYNTHESIS - PREPARATION OF MYOINOSITOL PHOSPHATES AND RELATED CYCLITOL DERIVATIVES FROM BENZENE

Pseudomonas putida oxidation of benzene affords cis-3,5-cyclohexadiene-1,2-diol (2) which is used as a novel precursor for the synthesis of D- and L-myo-inositol 1,4,5-trisphosphates, (-)-(1) and (+)-(1). The versatility of this approach to functionalised cyclitols is illustrated in the synthesis of -inositol l-phosphate (19), 6-deoxy, 6-deoxy-6-fluoro, and 6-deoxy-6-methyl myo- inositols (31), (37) and (43), and their 1,4,5-trisphosphate derivatives (33), (39) and (45). © 1990.