70 (R)-3-ヒドロキシ酪酸よりチエナマイシンおよび1β-メチルカルバペネムの合成研究

概要

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The key intermediates of thienamycin (1) and 1β-methylcarbapenem (2) were synthesized in an enantioselective manner from (R)-3-hydroxybutyrate (10). The reaction of the dianion of 10 with N-acylaldimine 11 gave predominantly (syn, anti)-product 12, which converted into the cyclic hemithio ketal 14. Inversion of the carboxyl group of 14 followed by oxidative hydrolysis gave Melillo's lactone 18 in an optically active form. The same methodology was applied successfully to synthesis of 2. Cyclization of 21 resulted in introduction of the fourth chiral center in a highly stereocontrolled fasion to yield a single isomer 23, which was derived into the lactone 27. Treatment of 27 with DCC furnished the β-lactam 29, which served as the key intermediate of 2.
天然有機化合物討論会の論文
1986-09-09