5-exo Radical cyclization onto 3-alkoxyketimino-1, 6-anhydromannopyranoses. Efficient preparation of synthetic intermediates for (-)-tetrodotoxin

B Noya; M D Paredes; L Ozores; R Alonso

doi:10.1021/jo000325y

5-exo Radical cyclization onto 3-alkoxyketimino-1, 6-anhydromannopyranoses. Efficient preparation of synthetic intermediates for (-)-tetrodotoxin

J Org Chem. 2000 Sep 22;65(19):5960-8. doi: 10.1021/jo000325y.

Authors

B Noya¹, M D Paredes, L Ozores, R Alonso

Affiliation

¹ Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15706 Santiago de Compostela, Spain.

PMID: 10987929
DOI: 10.1021/jo000325y

Abstract

Ketoxime ethers at C3 of 1,6-anhydro-beta-D-mannopyranose derivatives were found to be useful 5-exo radical traps of alkyl and vinyl radicals generated at a chain tethered to the C2 hydroxyl group, allowing advanced synthetic intermediates for (-)-tetrodotoxin to be prepared from D-mannose in good overall yield.

Publication types

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

MeSH terms

Alkylation
Cyclization
Mannose / analogs & derivatives*
Mannose / chemical synthesis*
Molecular Conformation
Morpholines / chemical synthesis
Morpholines / chemistry
Stereoisomerism
Tetrodotoxin / chemistry*
Vinyl Compounds / chemistry

Substances

Morpholines
Vinyl Compounds
Tetrodotoxin
Mannose