A concise synthesis of carbasugars isolated from Streptomyces lincolnensis

Suvi Holmstedt; Nuno R. Candeias

doi:10.1016/j.tet.2020.131346

A concise synthesis of carbasugars isolated from Streptomyces lincolnensis

Suvi Holmstedt, Nuno R. Candeias

Materials Science and Environmental Engineering

Research output: Contribution to journal › Article › Scientific › peer-review

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.

Original language	English
Article number	131346
Number of pages	6
Journal	Tetrahedron
Volume	76
Issue number	51
DOIs	https://doi.org/10.1016/j.tet.2020.131346
Publication status	Published - 2020
Publication type	A1 Journal article-refereed

Keywords

Carbasugar
Chiron
Cyclitol
Hemisynthesis
Quinic acid

Publication forum classification

Publication forum level 1

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2020.131346

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title = "A concise synthesis of carbasugars isolated from Streptomyces lincolnensis",

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",

author = "Suvi Holmstedt and Candeias, {Nuno R.}",

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language = "English",

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AU - Candeias, Nuno R.

PY - 2020

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N2 - (−)-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.

AB - (−)-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.

KW - Carbasugar

KW - Chiron

KW - Cyclitol

KW - Hemisynthesis

KW - Quinic acid

U2 - 10.1016/j.tet.2020.131346

DO - 10.1016/j.tet.2020.131346

M3 - Article

AN - SCOPUS:85086914275

SN - 0040-4020

VL - 76

JO - Tetrahedron

JF - Tetrahedron

IS - 51

M1 - 131346

ER -

A concise synthesis of carbasugars isolated from Streptomyces lincolnensis

Abstract

Keywords

Publication forum classification

ASJC Scopus subject areas

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