Stereoselective Synthesis of Cis-Substituted Azetidinones from Penicillin: a Formal Total Synthesis of Loracarbef

DOI: 10.1016/S0040-4039(00)93376-8

Source and publish data:

Tetrahedron Letters p. 3051 - 3054 (1993)

Update date:2022-08-05

Topics:

Authors:

Deeter, Jack B.

Hall, David A.

Jordan, Christopher L.

Justice, Richard M.

Kinnick, Michael D.

et al. et al.

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Article abstract of DOI:10.1016/S0040-4039(00)93376-8

A new method for the synthesis of chiral azetidinones bearing a carbon-carbon bond at the 4-position is described.The preparation involves a stereoselective alkylation-reduction of a silylated 4-phenylsulfonyl azetidinone.The utility of this method was demonstrated by a formal total synthesis of loracarbef.

Full text of DOI:10.1016/S0040-4039(00)93376-8

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Product name:N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-2-dodecyl-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide

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