Kirk L. Sorgi

A mild method for the synthesis of anomerically allylated C-glycopyranosides and C-glycofuranosides

The reaction of glycosyl acetates with allyltrimethylsilane in the presence of zinc bromide has been investigated as a new method for C-glycoside construction.

A Practocal Prepraration of D1-2-Substituted and D1-2,3-Disubstituted Pyrrolines

Addition of N-vinylpyrrolidinone and an ester to NaH in THF effects acylation and affords keto lactams (1) in high yields. Hydrolysis of 1 in strong acid generates Δ 1 -2-substituted pyrrolines (2) in good yield. Keto lactams (1) can be further alkylated and hydrolyzed to produce Δ 1 -2,3-disubstituted pyrrolines (4) in good isolated yield

The conversion of methyl pseudomonate C to pseudomonic acid A

Abstract A process for the conversion of methyl pseudomonate C to pseudomonic acid A with partial stereoselectivity is described.

Use of the anomeric allylation reaction in natural products synthesis - a stereocontrolled synthesis of methyl deoxypseudomonate B.

Abstract L -lyxose has been elaborated to methyl deoxypseudomonate B (I) by a sequence of reactions involving the Lewis acid catalyzed anomeric allylation procedure and a stereospecific Grignard addition reaction.

The Carroll rearrangement: A facile entry into substituted arylacetones and related derivatives

Abstract Acetoacetates, easily prepared from substituted p-quinols, undergo a mild room temperature Carroll rearrangement to afford substituted arylacetones and related derivatives in moderate to good yields.

Stereochemistry of the alkoxyselenation of substituted 3,4-dihydropyrans: a useful process for the construction of 2-alkoxy-5,6-dihydro-2H-pyrans

The stereochemistry of the alkoxyselenation of 3,4-dihydro-2H-pyrans has been examined as part of a study to identify new routes to monosaccharide components.