A novel and highly stereoselective synthesis of 2-substituted perhydrofuro[2,3-b]pyran derivatives

Xiaofeng Ma; Qiang Tian; Qin Tang; Jinzhong Zhao; Huawu Shao

doi:10.1021/ol201622t

A novel and highly stereoselective synthesis of 2-substituted perhydrofuro[2,3-b]pyran derivatives

Org Lett. 2011 Aug 19;13(16):4276-9. doi: 10.1021/ol201622t. Epub 2011 Jul 20.

Authors

Xiaofeng Ma¹, Qiang Tian, Qin Tang, Jinzhong Zhao, Huawu Shao

Affiliation

¹ Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.

PMID: 21774487
DOI: 10.1021/ol201622t

Abstract

An effective and facile method for the synthesis of 2-substituted perhydrofuro[2,3-b]pyran derivatives is described. The cyclization of 2-C-aldehydo-2-deoxy-D-thioglucoside in the presence of N-iodosuccinimide (NIS) is highly stereoselective. 2-Substituted cyclization products were obtained in good to excellent yields.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Glucosides / chemistry
Hydrogenation
Models, Molecular
Molecular Structure
Pyrans / chemical synthesis*
Stereoisomerism

Substances

Glucosides
Pyrans