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ChemInform Abstract: Synthesis of 2-(Hydroxymethyl)-1β-methylcarbapenem. Chemoselective Organometallic Addition to 3-Substituted 4-[(R)-1-Carboxyethyl]azetidin-2-one.

✍ Scribed by X. E. HU; T. P. JUN. DEMUTH

Publisher: John Wiley and Sons
Year: 2010
Weight: 38 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199830274

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✦ Synopsis

Synthesis of 2-(Hydroxymethyl)-1β-methylcarbapenem.

Chemoselective Organometallic Addition to 3-Substituted 4-[(R)-1-Carboxyethyl]azetidin-2-one.

-A new method to introduce the α-hydroxymethyl function at the 2-position of the carbapenem system in an early stage of the synthesis is investigated. Protected hydroxymethyl synthons are added to the lithium or magnesium salt of an azetidine carbocyclic acid in moderate yields up to 49%. The following synthesis of the carbapenem system leads to the products in overall yields of 12 -19%. The method is reproducible from a 0.5 to a 50 g scale. -(HU, X.

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