A new stereocontrolled synthetic route to (-)-echinosporin from D-glucose via Padwa allenylsulfone [3 + 2]-anionic cycloadditive elimination

Jakub T Flasz; Karl J Hale

doi:10.1021/ol301090v

A new stereocontrolled synthetic route to (-)-echinosporin from D-glucose via Padwa allenylsulfone [3 + 2]-anionic cycloadditive elimination

Org Lett. 2012 Jun 15;14(12):3024-7. doi: 10.1021/ol301090v. Epub 2012 May 30.

Authors

Jakub T Flasz¹, Karl J Hale

Affiliation

¹ The School of Chemistry and Chemical Engineering, and the CCRCB, Queen's University Belfast, Stranmillis Road, Belfast BT9 5AG, Northern Ireland, UK.

PMID: 22646909
DOI: 10.1021/ol301090v

Abstract

A new formal total synthesis of (-)-echinosporin has been developed based upon the Padwa [3 + 2]-cycloadditive elimination reaction of allenylsulfone 4 with the D-glucose-derived enone 14 which provides cycloadduct 12.

Publication types

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

MeSH terms

Alkadienes / chemistry*
Anions / chemistry
Cyclization
Esters / chemistry
Glucose / chemistry*
Lactones / chemical synthesis
Molecular Structure
Stereoisomerism
Sulfones / chemistry*

Substances

Alkadienes
Anions
Esters
Lactones
Sulfones
propadiene
echinosporin
Glucose