Showing papers by "Francesca Pelizzoni published in 1995"

Bioconversion of substituted naphthalenes to the corresponding 1,2-dihydro-1,2-dihydroxy derivatives. Determination of the regio- and stereochemistry of the oxidation reactions

Abstract: A mutant (TTC1) derived from Pseudomonas fluorescens N3 has been obtained for use in the bioconversion of several naphthalene derivatives to the corresponding optically active cis-dihydrodiols on a milligrams-to-grams scale. All main compounds have been characterized, their relative and absolute configuration assigned, and their enantiomeric purity determined. The regio- and stereoselectivity of the transformation has been established. The procedure therefore represents a valid method for the convenient preparation of a pool of valuable chiral syntons and auxiliaries.

Synthesis of C‐Glycosyl Compounds: The Reaction of Acetylated Glycals with tert‐Butoxycarbonylmethylzinc Bromide.

Abstract: There is increasing interest in C-glycosyl compounds because of their potential as enzyme inhibitors’ and chirons for the synthesis of complex natural products2. C-Glycosylation procedures variously involve sigmatropic rearrangements”, addition of a carbon nucleophile at an anomeric centre4, reactions of glycosyl radicals5 or carbanions”, and nucleophilic addition to glycals’. We now report on the reactions of the Reformatsky reagent tert-butoxycarbonylmethylzinc bromide with the acetylated glycals l-4. This reagent was chosen as a model since it is a stable, easily accessible, crystalline compound’, the CH,COO’Bu residue can be easily transformed, and a CH,COOH substituent is “bioisosteric” with a phosphate group’.