6533b7d3fe1ef96bd125fe0f
RESEARCH PRODUCT
ChemInform Abstract: Enantioselective Synthesis of Herbertane Sesquiterpenes: Synthesis of (-)-α-Formylherbertenol.
Remedios H. PerniConsuelo AgullóAntonio AbadAna C. Cuñatsubject
Benzaldehydechemistry.chemical_compoundEnantiopure drugChemistryStereochemistryArylSynthonRobinson annulationEnantioselective synthesisGeneral MedicineSesquiterpeneTrifluoromethanesulfonatedescription
Abstract The synthesis of 4-hydroxy-3-[(1 S )-1,2,2-trimethylcyclopentyl]benzaldehyde [(−)-α-formylherbertenol 1 ], a herbertane-type sesquiterpene isolated from the leafy liverwort Herberta adunca , from β-cyclogeraniol is described. The synthesis is based on the previously described preparation of an enantiopure 1,2,2-trimethylcyclopentane synthon from which the characteristic aromatic moiety of 1 is elaborated, using a Robinson annulation and a palladium-catalysed methoxycarbonylation of an aryl triflate as key synthetic steps. The synthesis of the natural sesquiterpene (−)-α-herbertenol, also a natural sequiterpene, using the same methodology is also described.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-06-03 | ChemInform |