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Synthesis of a protected 3,4-dihydroxyproline from a pentose sugar
1Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand.
Organic Letters
|May 24, 2000
Abstract:
[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.