126579-13-3Relevant academic research and scientific papers
A Novel Ring-Closure Strategy for the Carbapenems: The Total Synthesis of (+)-Thienamycin
Hanessian, Stephen,Desilets, Denis,Bennani, Youssef L.
, p. 3098 - 3103 (2007/10/02)
Intramolecular Michael cyclization of an N--4-(3-nitro-2-propenyl)-3-oxoazetidin-2-one available in optically pure form leads to the corresponding carbapenam skeleton.Further elaboration via oxidative cleavage of an exocyclic nitromethylene group gives an advanced intermediate, which was transformed into (+)-thienamycin.The stereochemistry of the Michael cyclization and the pitfalls of protective group chemistry are discussed.
