Transformation of D-Erythrose to Some Pseudoaldopentofuranoses. Syntheses of (1S,2R,3S,4S)-, (1R,2R,3S,4S)-, and (1R,2S,3S,4S)-2,3,4-Trihyroxy-1-(hydroxymethyl)cyclopentanes and (1R,2S,3R,4R)-2,3-Dihydroxy-4-(hydroxymethyl)-1-cyclopentanamine

Article abstract of DOI:10.1021/jo00242a016

Sodium borohydride reduction of (1S,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-3,4-(isopropylidenedioxy)-2-cyclopentanone (11), which was prepared from D-erythrose, proceeds exlusively from the β-face to provide 2R-hydroxyl derivative 12.Compound 12 is a derivative of carbocyclic analogue of β-L-lyxofuranose.Silica gel promoted configurational inversion at the branched carbon in 11 followed by sodium borohydride reduction provides 1R,2R diastereomer 17 and 12 a 2.8:1 ratio.The former is a protected form of carboxylic α-D-ribofuranose.Replacement of the mesyloxy group in 23, which was derived from 17, by a hydroxyl group in a S_N2 fashion and deprotection of the product followed by acetylation gave a derivative of carbocyclic α-D-xylofuranose 24.Compound 17 was also converted to compound 7, a key intermediate for the synthesis of the carboxylic nucleoside antibiotic (-)-aristeromycin (1), via a S_N2 replacement of the mesyloxy group in 26 by an azide group.