Acetalization/ring-closing metathesis for synthesis of tetrahydropyran containing natural products thromboxane B2 and spicamycin

ORGN 728

Christopher C Marvin, cmarvin@chem.wisc.edu, Alexander J. L. Clemens, ajclemens@wisc.edu, Michael P. McGuan, and Steven D. Burke, burke@chem.wisc.edu. Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706
Acetalization of C2 symmetric 3,4-dihydroxy-1,5-hexandienes with unsaturated aldehydes (or transacetalization with acetals) followed by ring-closing metathesis allows rapid access to the 6,8-dioxabicyclo[3.2.1]oct-2-ene ring system. The rigidity of this system combined with exo/endo facial selectivity enables stereocontrolled synthesis. Efforts to elaborate these bridged ring systems into tetrahydropyran containing natural products thromboxane B2 and spicamycin will be described.

 

Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006