title: Toward the synthesis of phomoidride D.
abstract: An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels-Alder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: Graham K
authors.initials: GK
authors.lastname: Murphy
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Shirahata
authors.forename: Naoto
authors.initials: N
authors.lastname: Hama
authors.forename: Aaron
authors.initials: A
authors.lastname: Bedermann
authors.forename: Ping
authors.initials: P
authors.lastname: Dong
authors.forename: Travis C
authors.initials: TC
authors.lastname: McMahon
authors.forename: Barry M
authors.initials: BM
authors.lastname: Twenter
authors.forename: David A
authors.initials: DA
authors.lastname: Spiegel
authors.forename: Ivar M
authors.initials: IM
authors.lastname: McDonald
authors.forename: Nobuaki
authors.initials: N
authors.lastname: Taniguchi
authors.forename: Munenori
authors.initials: M
authors.lastname: Inoue
authors.forename: John L
authors.initials: JL
authors.lastname: Wood
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D008299:Maleic Anhydrides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001688:Biological Products; D001643:Bridged Bicyclo Compounds; D008299:Maleic Anhydrides; C438971:phomoidride D