A stereocontrolled, enantiomerically specific total synthesis of thienamycin

Abstract
A versatile stereocontrolled total synthesis of thienamycin starting from L-aspartic acid is reported. Stereocontrol is achieved by potassium tri-$sec$-butylborohydride reduction of a thermodynamically formed 3$\alpha$-acetylazetidinone intermediate. The key [3. 2. 0] bicyclic ring system is prepared by a metal catalyzed carbene insertion reaction.

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