Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol

Jing Zeng; Seenuvasan Vedachalam; Shaohua Xiang; Xue-Wei Liu

doi:10.1021/ol102473k

Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol

Org Lett. 2011 Jan 7;13(1):42-5. doi: 10.1021/ol102473k. Epub 2010 Nov 29.

Authors

Jing Zeng¹, Seenuvasan Vedachalam, Shaohua Xiang, Xue-Wei Liu

Affiliation

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.

PMID: 21114334
DOI: 10.1021/ol102473k

Abstract

A mild, stereoselective, and quick approach to accessing alkynyl and alkenyl C-glycosides via BF(3)·Et(2)O 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.

Publication types

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

MeSH terms

Benzyl Alcohols / chemical synthesis*
Borates / chemistry*
Fluorides / chemistry*
Fluorine Compounds / chemistry*
Furans / chemical synthesis*
Glycosylation
Molecular Structure
Stereoisomerism

Substances

Benzyl Alcohols
Borates
Fluorine Compounds
Furans
varitriol
Fluorides