Application of α-hydroxy phosphonates to the synthesis of cyclic ether-containing natural products

ORGN 717

Nongnuch Sutivisedsak, nuchchula@yahoo.com and Christopher D. Spilling. Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Blvd., St. Louis, MO 63121
Allylic hydroxy phosphonates are versatile intermediates for the asymmetric synthesis of natural products and enzyme inhibitors. A variety of substituted allylic hydroxy phosphonates and the carbonate derivatives can be prepared via cross metathesis of phosphonates 1 and 2 with substituted alkenes. The stereospecific palladium catalyzed addition of oxygen nucleophiles to phosphono allylic carbonates results in the efficient stereoselective synthesis of tetrahydrofurans and pyrans; the useful nonracemic building blocks for the synthesis of biologically active molecules.