title: Total synthesis of ramonanins A-D.
abstract: The first total synthesis of the ramonanin family of lignan natural products is described. The short synthesis involves a 2,5-diaryl-3,4-dimethylene tetrahydrofuran intermediate, which participates in an unexpectedly facile Diels-Alder dimerization, generating all four natural products. Insights into the reactivity and stereoselectivity of the key dimerization are provided through computational studies employing B3LYP/6-31G(d) and M06-2X/6-31G(d) model chemistries.
authors.affiliation: Research School of Chemistry, Australian National University, Canberra, ACT 2601 (Australia).
authors.forename: Ross S
authors.initials: RS
authors.lastname: Harvey
authors.forename: Emily G
authors.initials: EG
authors.lastname: Mackay
authors.forename: Lukas
authors.initials: L
authors.lastname: Roger
authors.forename: Michael N
authors.initials: MN
authors.lastname: Paddon-Row
authors.forename: Michael S
authors.initials: MS
authors.lastname: Sherburn
authors.forename: Andrew L
authors.initials: AL
authors.lastname: Lawrence
mesh_terms: D001688:Biological Products / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D017705:Lignans
keywords: Diels-Alder reactions; biomimetic synthesis; enyne metathesis; lignans; natural products