Synthesis of 3-(polyacetoxyalkyl)pyrroles from 3-aminocrotonic esters and open-chain sugar nitro-olefins

Abstract

D-gluco- and D-galacto-3,4,5,6,7-Penta-acetoxy-1-nitrohept-1-ene (1 a and b) reacted with 3-(alkylamino)crotonic esters (2) yielding the Michael-type adducts (3) which have a preference for the intramolecularly bonded (Z)-configuration. These compounds were cyclized into 4-(D-gluco- or D-galacto-penta-acetoxypentyl)-1-alkyl-2-methylpyrrole-3-carboxylic esters (5), the O-deacetylation of which afforded the corresponding polyols (8). Periodate or lead tetra-acetate oxidation of (8) gave the pyrrole-3-carbaldehydes (9).