Stereoselective synthesis of 5-O-carbamoylpolyoxamic acid by [2,3]- Wittig-Still rearrangement

Article abstract of DOI:10.1016/S0040-4020(99)00838-8

Stereoselective [2,3]-Wittig rearrangement of E- and Z-allylic stannyl ethers derived from an isopropylidene L-threitol derivative has been investigated. The E-isomer exhibited best diastereoselectivity and the resulting rearrangement product has been converted to protected polyoxamic acid, an amino acid component of many bioactive polyoxins.