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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… Click to show full abstract
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:
synthesis carbasugars;
isolated streptomyces;
concise synthesis;
carbasugars isolated;
streptomyces lincolnensis
Journal Title: Tetrahedron
Year Published: 2020
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Journal Title: Tetrahedron
Year Published: 2020
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!