Template-directed C-H insertion: synthesis of the dioxabicyclo[3.2.1]octane core of the zaragozic acids.
[reaction: see text] The preparation of (+/-)-24, a model for the core of the zaragozic acids, is reported. The pivotal reaction in this endeavor is the dirhodium(II)-catalyzed intramolecular C-H bond insertion of 2-diazoacetyl-1,3-dioxane 4, a transformation which generates four of the six stereocenters present in the core structure. A novel method for the diastereoselective synthesis of pyruvic acid acetals was also developed and employed in the preparation of 4 from xylitol derivative 7.
Wardrop
D J
DJ
Department of Chemistry, University of Illinois at Chicago, 60607-7061, USA. wardropd@uic.edu
Velter
A I
AI
Forslund
R E
RE
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D009795:Octanes / Q000138:chemical synthesis*; D014233:Tricarboxylic Acids / Q000138:chemical synthesis*
D019086:Bridged Bicyclo Compounds, Heterocyclic; D009795:Octanes; D014233:Tricarboxylic Acids