Abstract: cis-Toluenediol obtained by the microbial degradation of toluene by Pseudomonas putida 390 was shown to be a versatile chiral pool substrate in the formal total synthesis of PGEp. Diol 1 was converted to enone 5 in three steps in an overall yield of 45%. A method for reliable oxidative cleavage of 1, 3-dienes to 1, 4-dicarbonyl compounds was implemented. Other transformations of 1 leading to terpenoid or cyclohexene oxide ...
