A concise synthesis of carbasugars isolated from Streptomyces lincolnensis

TETRAHEDRON

卷:76

Article

Holmstedt, Suvi¹  Candeias, Nuno R.^1,2 

[1] Tampere Univ, Fac Engn & Nat Sci, Tampere 33101, Finland

[2] Univ Aveiro, Dept Chem, LAQV REQUIMTE, P-3810193 Aveiro, Portugal

关键词: Carbasugar;    Chiron;    Cyclitol;    Hemisynthesis;    Quinic acid;   

DOI  :  10.1016/j.tet.2020.131346

来源: Elsevier

【 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.

【 授权许可】

Free