Chemical-enzymatic synthesis of azasugar phosphonic acids as glycosyl phosphate surrogates

Starting from achiral materials two stereoisomeric phosphonylated dihydroxy pyrrolidines containing four stereogenic centers were synthesized enantiose lectively employing a combination of enzymatic and transition-metal-mediate d methods. Both compounds contain features of the transition state of the e nzyme-catalyzed fucosyl transfer reaction and represent building blocks of potential inhibitors against this class of enzymes. (C) 2001 Elsevier Scien ce Ltd. All rights reserved.