pukalide has been researched along with furan* in 2 studies
2 other study(ies) available for pukalide and furan
| Article | Year |
|---|---|
Total Synthesis of 7-epi-Pukalide and 7-Acetylsinumaximol B.
Convergent total syntheses of the furanocembranoids 7-epi-pukalide and 7-acetylsinumaximol B have been achieved using a one-pot Knoevenagel condensation and thioether-mediated furan-forming reaction. Furan formation proceeds via a sulfur ylide and results in rapid introduction of structural complexity during the coupling of two highly functionalised fragments. The targets have been prepared in 16 steps from (R)-perillyl alcohol. Topics: Diterpenes; Epoxy Compounds; Furans; Monoterpenes; Stereoisomerism | 2017 |
Synthesis of (-)-deoxypukalide, the enantiomer of a degradation product of the furanocembranolide pukalide.
A convergent stereoselective synthesis of (-)-deoxypukalide is described. This substance has not yet been found in Nature but is obtained through deoxygenation of pukalide, the first naturally occurring furanocembrane to be structurally elucidated. The route features a new intraannular furan synthesis that entails treatment of a 4-oxopropargylic beta-keto ester with silica gel. The product of this novel reaction, a 3-carboxy 2,5-bridged furan, is formed in 96% yield. The synthetic strategy was strongly directed by molecular mechanics calculations, which provided valuable insight into stereodefining steps including double bond stereochemistry and butenolide configuration. Topics: Animals; Bridged-Ring Compounds; Cnidaria; Epoxy Compounds; Furans; Models, Molecular; Molecular Conformation; Stereoisomerism; Terpenes; Thermodynamics | 2001 |