Rapid synthesis of the 7-deoxy zaragozic acid core.
[reaction: see text] We have developed an efficient synthesis of the 7-deoxy zaragozic acid core. The synthesis begins with a Feist-Bénary reaction that assembles all three carbons of the polycarboxylic acid portion of the core. This reaction is followed by highly diastereoselective aldol and dihydroxylation reactions that set the remaining stereocenters of the core. The synthesis finishes with lactol oxidation and lactone alcoholysis/ketal formation reactions to construct the bicyclic ring system of the core.
Calter
Michael A
MA
Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA. calter@chem.rochester.edu
Zhu
Cheng
C
Lachicotte
Rene J
RJ
D000935:Antifungal Agents / Q000138:chemical synthesis*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D013237:Stereoisomerism; D014233:Tricarboxylic Acids / Q000138:chemical synthesis*
D000935:Antifungal Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D014233:Tricarboxylic Acids; C075117:squalestatin 1