Journal of Organic Chemistry p. 3098 - 3103 (1990)
Update date:2022-07-30
Topics:
Hanessian, Stephen
Desilets, Denis
Bennani, Youssef L.
Intramolecular Michael cyclization of an N-<(alkoxycarbonyl)methyl>-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.
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