Stereoselective synthesis of myo-inositol via ring-closing metathesis: a building block for glycosylphosphatidylinositol (GPI) anchor synthesis

Rosemary M Conrad; Michael J Grogan; Carolyn R Bertozzi

doi:10.1021/ol025680k

Stereoselective synthesis of myo-inositol via ring-closing metathesis: a building block for glycosylphosphatidylinositol (GPI) anchor synthesis

Org Lett. 2002 Apr 18;4(8):1359-61. doi: 10.1021/ol025680k.

Authors

Rosemary M Conrad¹, Michael J Grogan, Carolyn R Bertozzi

Affiliation

¹ Department of Chemistry, Center for New Directions in Organic Synthesis, University of California, Berkeley, CA 94720.

PMID: 11950362
DOI: 10.1021/ol025680k

Abstract

Here we report a concise stereoselective synthesis of myo-inositol via ring-closing metathesis. A readily available bis-Weinreb amide of D-tartrate served as a key intermediate. [reaction: see text]

Publication types

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

MeSH terms

Animals
Carbohydrate Sequence
Erythrocytes / enzymology
Glycosylphosphatidylinositols / chemical synthesis*
Indicators and Reagents
Inositol / chemical synthesis*
Inositol / chemistry
Stereoisomerism
Trypanosoma brucei brucei / chemistry

Substances

Glycosylphosphatidylinositols
Indicators and Reagents
Inositol