Tetrahedron Letters p. 1857 - 1860 (1987)
Update date:2022-07-31
Topics:
Prasad, J. Siva
Liebeskind, Lanny S.
A highly stereoselective route to precursors of 1β-methylcarbapenems is described.Hydride reduction of a hexacarbonyldicobalt stabilized propargyl cation derived from a 4-acyl-2-azetidinone prepared using the Weinreb ketone synthesis proceeds with complete stereochemical control to a 1β-methylcarbapenem precursor bearing an alkynyl unit.The alkyne is readily elaborated to (3S,4R)-3-<(1R)-1-t-butyldimethylsilyloxyethyl>-4-<(1R)-1-methyl-3-methoxycarbonyl-2-oxopropyl>-2-azetidin-2-one or hydrogenated and oxidatively cleaved to (3S,4S)-3-<(1R)-1-t-butyldimethylsilyloxyethyl>-4-<(1R)-1-carboxyethyl>-azetidin-2-one.
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Doi:10.1271/bbb1961.51.2055
(1987)Doi:10.1021/jo00245a020
(1988)Doi:10.1002/jhet.2792
(2017)Doi:10.1055/s-1987-28057
(1987)Doi:10.1016/S0040-4039(00)96308-1
(1987)Doi:10.1021/jo00245a036
(1988)
