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Free-radical annelation in the synthesis of bicyclic β-lactams. 5. Synthesis of carbapenams

✍ Scribed by Mario D. Bachi; Alain De Mesmaeker; Nadine Stevenart-De Mesmaeker

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
204 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

Homolytic cyclization of some alkenyl fi-lactams afforded carbapenams, by exo addition, when a vicinally disubstituted double double bond was involved, and carbacephams, by endo addition, when a terminal double bond was involved. Some years ago, we described the synthesis of the (f)-1-oxacepham and (k)-1-oxahomocepham systems.'

The key reaction in that synthesis involved the completion of the bicyclic /I-lactam backbone through the intramolecular addition of a carbon-centered free radical to a carbon-carbon multiple bond.

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