Journal of the Chemical Society. Perkin transactions I p. 2029 - 2039 (1996)
Update date:2022-08-05
Topics:
Jackson, P. Mark
Roberts, Stanley M.
Davalli, Silvia
Donati, Daniele
Marchioro, Carla
Perboni, Alcide
Proviera, Stefano
Rossi, Tino
Coupling the silyl enol ether 5 and the β-lactam 9 (R = Me3Si) affords the ketones 13a-d. Compounds 13a, 13c and 13d are converted into the tricyclic lactams 16-20, 23-25. (Chemoenzymatic synthesis of optically pure silyl enol ether 5 gave access to homochiral lactams 23-25.) In addition the ketoazetidinones 13 are protected as the 1,3-oxazanes 30. A hydroxyethyl moiety is introduced into these oxazanes at C-11 with the desired stereochemistry using the Bouffard methodology, to afford the alcohols 32. Formation of the corresponding nitrobenzyl carbonate, deprotection and oxidation furnishes the ketones 35a and 35b, which are subsequently converted into the trinems 41a and 41b, respectively.
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