title: Total synthesis of (±)-distomadines A and B.
abstract: The total synthesis of distomadines A and B, two structurally unique tetracyclic quinolines, is described. The route features a three-step process to access the pyranoquinoline butenolide rings via a Suzuki cross coupling of a 5-bromo-4-methoxycarbonylmethoxyquinoline with a vinyl boronate, followed by an α-ketohydroxylation and double cyclization by intramolecular aldol condensation and lactonization. Subsequent manipulation of the side chain to introduce the guanidine fragment completed the synthesis of distomadine B, whereas the distomadine A congener resulted from decarboxylation of a late-stage intermediate.
authors: School of Chemistry, University Park, University of Nottingham , Nottingham NG7 2RD, U.K.
authors: Alexandre E R
authors: AE
authors: Jolibois
authors: William
authors: W
authors: Lewis
authors: Christopher J
authors: CJ
authors: Moody
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D018360:Crystallography, X-Ray; D003500:Cyclization; D003653:Decarboxylation; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D011804:Quinolines; C588338:distomadine A; C116609:3-hydroxybutanal