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Direct C-Glycosylation of Organotrifluoroborates with Glycosyl Fluorides and Its Application to the Total Synthesis of (+)-Varitriol

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Jing Zeng, Seenuvasan Vedachalam, Shaohua Xiang, and Xue-Wei Liu*

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371

Org. Lett., 2011, 13 (1), pp 42–45

DOI: 10.1021/ol102473k

Publication Date (Web): November 29, 2010

xuewei@ntu.edu.sg

Section:

Carbohydrates

Abstract

A mild, stereoselective, and quick approach to accessing alkynyl and alkenyl C-glycosides via BF₃·Et₂O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

N-Heterocyclic Carbene Catalyzed C-Glycosylation: A Concise Approach from Stetter Reaction
Seenuvasan Vedachalam, Shi Min Tan, Hui Ping Teo, Shuting Cai, and Xue-Wei Liu
Organic Letters2012 14 (1), 174-177
- N-Heterocyclic Carbene Catalyzed C-Glycosylation: A Concise Approach from Stetter Reaction
  Seenuvasan Vedachalam, Shi Min Tan, Hui Ping Teo, Shuting Cai, and Xue-Wei Liu
  Organic Letters2012 14 (1), 174-177
  Described herein is the first example of an organocatalytic approach for acylanion addition to the anomeric carbon of 2-nitroglucal using an N-heterocyclic carbene catalyst. Control over the reaction conditions gives β-selective and nitro-eliminated C-...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Regio- and Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides via Palladium Catalyzed Decarboxylative Reactions
Shaohua Xiang, Shuting Cai, Jing Zeng, and Xue-Wei Liu
Organic Letters2011 13 (17), 4608-4611
- Regio- and Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides via Palladium Catalyzed Decarboxylative Reactions
  Shaohua Xiang, Shuting Cai, Jing Zeng, and Xue-Wei Liu
  Organic Letters2011 13 (17), 4608-4611
  An efficient and versatile approach for the synthesis of 2-deoxy-C-aryl glycosides is reported. This strategy is based on a palladium-catalyzed decarboxylative Heck coupling reaction of benzoic acids and glycals. A wide variety of glycals and benzoic ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links