title: Cycloaldol approach to the isobenzofuran core of eunicellin diterpenes.
abstract: [reaction: see text] A novel cycloaldol approach to the isobenzofuran core common to many of the eunicellin diterpenes is described. The cycloaldol precursor was prepared by aldol addition of (S)-(+)-carvone and methacrolein followed by etherification to a glycolate ester. Chemoselective enolization of the glycolate ester led to the cycloaldol adduct in high yield and diastereoselectivity. An oxidative rearrangement-allylic diazene rearrangement sequence established the requisite cis ring fusion.
authors.affiliation: Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, USA.
authors.forename: Yonghai
authors.initials: Y
authors.lastname: Chai
authors.forename: David A
authors.initials: DA
authors.lastname: Vicic
authors.forename: Matthias C
authors.initials: MC
authors.lastname: McIntosh
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; C476503:eunicellin