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

A novel and practical total synthesis of a tricyclic β-lactam antibiotic, GV104326 (4-methoxytrinem or Sanfetrinem) has been achieved in nine steps and about 33% overall yield from a commercially available acetoxyazetidinone chiron. A key step in the highly diastereoselective synthesis is a protonat...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 118; no. 41; pp. 9884 - 9891
Main Authors Hanessian, Stephen, Rozema, Michael J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.10.1996
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
1-BETA-METHYLCARBAPENEM
ENANTIOSELECTIVE PROTONATION
KEY INTERMEDIATE
PENEMS
DIASTEREOSELECTIVE PROTONATION
THIENAMYCIN
BIOLOGICAL EVALUATION
CARBANIONS
DERIVATIVES
STEREOCONTROLLED SYNTHESIS
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Summary:A novel and practical total synthesis of a tricyclic β-lactam antibiotic, GV104326 (4-methoxytrinem or Sanfetrinem) has been achieved in nine steps and about 33% overall yield from a commercially available acetoxyazetidinone chiron. A key step in the highly diastereoselective synthesis is a protonation of a zinc enolate complex which circumvents the use of enantiomerically pure (S)-2-methoxycyclohexanone. A mechanistic rationale is presented and experimentally verified.
Bibliography:Abstract published in Advance ACS Abstracts, September 15, 1996.
istex:E5657892DE9F8D9845639542F9D2B6879AE49C93
ark:/67375/TPS-TPQ17P24-Z
ISSN:0002-7863
1520-5126
DOI:10.1021/ja962006n