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A concise synthesis of carbasugars isolated from Streptomyces lincolnensis

Research output: Contribution to journalArticleScientificpeer-review

Details

Original languageEnglish
Article number131346
Number of pages6
JournalTetrahedron
DOIs
Publication statusE-pub ahead of print - 2020
Publication typeA1 Journal article-refereed

Abstract

(−)-Quinic acid was used as a starting material in the hemisynthesis of two epimeric carbasugars isolated from Streptomyces lincolnensis. Previous 10–12 steps syntheses for the carbasugars have been herein shortened to 4–6 steps by using quinic acid as a chiron, based on a regioselective reduction step, with stereoinversion of a tertiary center. Both C-5 epimers of (1R, 2R, 3R)-5-(hydroxymethyl)cyclohexane-1,2,3-triol were obtained in up to 76% overall yield.

Keywords

  • Carbasugar, Chiron, Cyclitol, Hemisynthesis, Quinic acid

Publication forum classification

Field of science, Statistics Finland