An expedient approach to the total synthesis of (+)-5-epi-eudesm-4(15)-ene-1β,6β-diol.
The first total synthesis of (+)-5-epi-eudesm-4(15)-ene-1β,6β-diol has been achieved in 12 steps starting from the known (-)-cis-piperitol and by using a chelation controlled glycolate enolate Ireland-Claisen rearrangement and an intramolecular nitrile oxide dipolar cycloaddition as key steps.
Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, 1211 Geneva 4, Switzerland.
Gowrisankar
G
Parthasarathy
Céline
C
Besnard
E Peter
EP
Kündig
D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D032862:Litsea / Q000737:chemistry; D008968:Molecular Conformation; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D045787:Sesquiterpenes, Eudesmane / Q000138:chemical synthesis*; D013237:Stereoisomerism
C579182:(+)-5-epi-eudesm-4(15)-ene-1beta,6beta-diol; D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane