The Enantioselective Synthesis of Some Useful Antibiotics based on the Chemicoenzymatic Strategy.

点击翻译按钮获取中文摘要

Since 1978, we have begun to synthesize biologically active natural products by a reasonable combination of enzymatic process (pig liver esterase, PLE) and usual organic synthesis and developed a new avenue for natural product synthesis. Our synthetic strategy for obtaining various antibiotics has therefore been designed as follows.(1) Retrosynthesis is performed to generate, from the target molecule, a symmetric diester in the prochiral or meso form.(2) The symmetric diester is subjected to asymmetric hydrolysis with pig liver esterase to generate the corresponding chiral half-ester. (enzymatic conversion of <sigma> -symmetry to <C_1> -symmetry)(3) The chiral half-ester is converted to the target molecule by means of organic synthesis. The total strategy is called "Symmetrization-asymmetrization Concept".Thus, in addition to various carbapenem antibiotics and nucleosides, fortimicin A and part of rhizoxin were synthesized and the results were presented at various famous international meetings of the world.