title: Synthesis of balsaminone A, a naturally occurring pentacyclic dinaphthofuran quinone.
abstract: A short synthesis of the natural product balsaminone A, a dinaphthofuran quinone, is described. The key steps of the synthesis are base-induced coupling of 1,4-dihydroxy-2-naphthaldehyde with 2,3-dichloronaphthoquinone to give a pentacyclic dinaphthofuran directly, followed by conversion of the aldehyde into the desired methoxy group via the corresponding phenol. The synthesis, in which the structure of a key pentacyclic intermediate is corroborated by X-ray crystallography, confirms the original structural assignment of the natural product.
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.
authors.forename: Jalindar
authors.initials: J
authors.lastname: Padwal
authors.forename: William
authors.initials: W
authors.lastname: Lewis
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Moody
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001688:Biological Products; D009285:Naphthoquinones; C115539:balsaminone A