61 ペニシリンからペネム、カルバペネムへ : チエナマイシンの合成

概要

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6,6-Bis(phenylselenyl)penicillanate 3 was converted into 6-1'-(R)-hydroxyethyl substituted penicillanate 4_R in high yield. Compound 4_R was deselenylated to 5. Oxidation, and then the basic epimerization of the cis sulfone 6 gave trans sulfone derivative 7. The trans sulfone 7 was degraded to the monocyclic β-lactams 9 and 10a, b. The sequence of the reactions was applicable to the compound 11 to give the same monocyclic β-lactam 9. These monocyclic β-lactams and 14 were converted into 4-cyano derivative (C_1-unit introduction ) under two phase reaction conditions. The cyano group in 15 was successively transformed into 17-22. The compound 22 was transformed via the trans-iodopropenylation method into the β-keto ester (32a,b) which is the important precursor for the synthesis of the carbapenem derivatives, and actually transformed into thienamycin (1).
天然有機化合物討論会の論文
1983-09-15