Total synthesis of thienamycin: a new approach from aspartic acid

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Abstract

A practical stereospecific synthesis of thienamycin 1 has been achieved. Key steps include a lead tetracetate oxidative decarboxylation and subsequent insertion of a four carbon diazo containing unit into a 3-acetoxy-2-azetidinene.

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    Citation Excerpt :

    Thus, a key transformation in our synthesis was to be an unprecedented double-diastereoselective condensation of a carbonate equivalent with the commercially available azetidinone (28). The diastereoselective addition of enolates to azetidinones is known, and has been used in our synthesis of imipenem [45]. However, this transformation needed to be re-engineered in this case to enable the formation of two stereocenters instead of one.

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