Enantioselective synthesis through microbial oxidation of arenes. 1. Efficient preparation of terpene and prostanoid synthons

T Hudlicky, H Luna, G Barbieri…

Index: Hudlicky; Luna; Barbieri; Kwart Journal of the American Chemical Society, 1988 , vol. 110, # 14 p. 4735 - 4741

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Citation Number: 145

Abstract

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 ...