A stereocontrolled, enantiomerically specific total synthesis of thienamycin.
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.
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D007769:Lactams / Q000138:chemical synthesis; D013237:Stereoisomerism; D013845:Thienamycins
D000900:Anti-Bacterial Agents; D007769:Lactams; D013845:Thienamycins; C015537:thienamycin