Divergent pathways to furosesquiterpenes: first total syntheses of (+)-zedoarol and (Rac)-gweicurculactone

Elissavet E Anagnostaki; Vera P Demertzidou; Alexandros L Zografos

doi:10.1039/c4cc09298h

Divergent pathways to furosesquiterpenes: first total syntheses of (+)-zedoarol and (Rac)-gweicurculactone

Chem Commun (Camb). 2015 Feb 11;51(12):2364-7. doi: 10.1039/c4cc09298h.

Authors

Elissavet E Anagnostaki¹, Vera P Demertzidou, Alexandros L Zografos

Affiliation

¹ Aristotle University of Thessaloniki, Department of Chemistry, Laboratory of Organic Chemistry, University Campus, 54124 Thessaloniki, Greece. alzograf@chem.auth.gr.

PMID: 25564049
DOI: 10.1039/c4cc09298h

Abstract

A non-natural hydroxy-elemane was found amenable to divergent transformations, producing either polyunsaturated guaianes under basic, oxygen-free conditions, or oxidized furogermacranes when anionic oxy-Cope reaction quenched by an oxidant is employed. Based on these findings, the first total syntheses of zedoarol and gweicurculactone are reported.

Publication types

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

MeSH terms

Azulenes / chemical synthesis*
Azulenes / chemistry
Furans / chemistry
Lactones / chemical synthesis*
Lactones / chemistry
Oxidation-Reduction
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / chemistry
Sesquiterpenes, Guaiane / chemistry
Stereoisomerism

Substances

Azulenes
Furans
Lactones
Sesquiterpenes
Sesquiterpenes, Guaiane
guaiane
zedoarol
gweicurculactone
furan