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ChemInform Abstract: A Highly Stereoselective and Practical Total Synthesis of the Tricyclic β-Lactam Antibiotic GV104326 (4-Methoxytrinem).

✍ Scribed by S. HANESSIAN; M. J. ROZEMA

Publisher: John Wiley and Sons
Year: 2010
Weight: 38 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199708224

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✦ Synopsis

A Highly Stereoselective and Practical Total Synthesis of the Tricyclic β-Lactam Antibiotic GV104326 (4-Methoxytrinem).

-The title compound (IX) is prepared in ∼ = 33% overall yield by a method which circumvents the use of enantiomerically pure (S)-2-methoxycyclohexanone. The key step is represented by the diastereoselective protonation of a Zn enolate from (VII) within an epimerization sequence to yield (VIII). -(HANESSIAN,

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