6533b7dafe1ef96bd126e069
RESEARCH PRODUCT
Ultrasound assisted reductive cleavage of eudesmane and guaiane γ-enonelactones. Synthesis of 1α,7α,10αH-guaian-4,11-dien-3-one and hydrocolorenone from santonin
Begoña GarcíaVictoria BarguesLuz CardonaGonzalo BlayJosé R. Pedrosubject
Terpenechemistry.chemical_compoundchemistryReductive cleavageOrganic ChemistryDrug DiscoveryUltrasound assistedSesquiterpeneBiochemistryMedicinal chemistrySantoninSonochemistrydescription
Abstract Ultrasound enhances the rate of reductive cleavage of the C6–oxygen bond of sesquiterpene enonelactones. trans-Eudesmanolides 1c–1g, cis-eudesmanolides 2a–2c, and trans-guaianolides 4a–4d react with Zn in acetic acid–H2O under sonochemical conditions to afford the corresponding sesquiterpene acids 3a–3g and 5a–5d, respectively in good yields. Starting from 5d two natural guaianes 1α,7α,10αH-guaian-4,11-dien-3-one (6) and hydrocolorenone (7) have been prepared in good yields through a straightforward sequence.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2001-11-01 | Tetrahedron |