title: A convergent and stereocontrolled cycloaddition strategy toward eudesmane sesquiterpenoid: total synthesis of (±)-6β,14-epoxyeudesm-4(15)-en-1β-ol.
abstract: We present in this report the development of a convergent and highly stereocontrolled cycloaddition strategy toward the synthesis of C-1, C-6, and C-14 tris-oxygenated eudesmane sesquiterpenoids. This approach was demonstrated in the first total synthesis of (±)-6β,14-epoxyeudesm-4(15)-en-1β-ol (1), a structurally unique ethereal eudesmane sesquiterpenoid, via an effective Diels-Alder construction of a compact functionalized tricycle intermediate from readily available N-benzylfurfurylamine (2) and homoprenyl maleic anhydride (3) as the C(5) and C(10) building blocks, respectively.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.
authors.forename: Cui-Cui
authors.initials: CC
authors.lastname: Wang
authors.forename: Wei-Dong Z
authors.initials: WD
authors.lastname: Li
mesh_terms: D003500:Cyclization; D015394:Molecular Structure; D045787:Sesquiterpenes, Eudesmane / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C575051:6beta,14-epoxyeudesm-4(15)-en-1beta-ol; D045787:Sesquiterpenes, Eudesmane; C015872:eudesmane