Synthesis of a protected 3,4-dihydroxyproline from a pentose sugar.
[reaction: see text] D-Ribonolactone (6) was transformed into N-((fluorenylmethoxy)carbonyl)-3,4-bis-O-(tert-butyldimethylsilyl)-D-2,3-cis-3,4-cis-3,4-dihydroxyproline (13) in nine chemical steps. This represents a potentially general strategy for the synthesis of 3,4-dihydroxyprolines, utilizing the pentose sugar series as starting materials.
Weir
C A
CA
Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand.
Taylor
C M
CM
D017607:Aluminum Compounds; D000818:Animals; D001372:Aza Compounds / Q000737:chemistry; D006909:Hydroxyproline / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D018020:Lithium Compounds; D009682:Magnetic Resonance Spectroscopy; D010429:Pentoses / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C026216:3,4-dihydroxyproline; D017607:Aluminum Compounds; D001372:Aza Compounds; D007202:Indicators and Reagents; D018020:Lithium Compounds; D010429:Pentoses; C042073:lithium aluminum hydride; D006909:Hydroxyproline