The chiral bicyclic β-keto ester (14), which is synthesised by our methods involving stereoselective differentiation between two identical groups in the diamide (4) of (R)-4-methoxycarbonyl-1,3-thiazolidine-2-thione and regiocontrolled Dieckmann-type cyclisation of half-thiol diester (11), has been successfully converted into (+)-carbacyclin (2).
Y. Nagao, T. Nakamura, M. Ochiai, K. Fuji and E. Fujita, J. Chem. Soc., Chem. Commun., 1987, 267 DOI: 10.1039/C39870000267
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