A concise synthesis of carbasugars isolated from Streptomyces lincolnensis

[摘要] (-)-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. (C) 2020 Elsevier Ltd. All rights reserved.

[发布日期] 2020-12-18

[关键词] Carbasugar;Chiron;Cyclitol;Hemisynthesis;Quinic acid