title: Modular Total Syntheses of the Alkaloids Discoipyrroles A and B, Potent Inhibitors of the DDR2 Signaling Pathway.
abstract: The title natural product 1 has been synthesized by treating the 1,2,3,5-tetrasubstituted pyrrole 23 with oxoperoxymolybdenum(pyridine) (hexamethylphosphoric triamide) (MoOPH). Compound 23 was itself prepared in seven steps from parent pyrrole using Ullmann-Goldberg and Suzuki-Miyaura cross-coupling, Vilsmeier-Haack formylation, electrophilic bromination, and Wittig olefination reactions as key steps. Related chemistry has been used to prepare discoipyrrole B (2).
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Yiwen
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Paul D
authors.initials: PD
authors.lastname: Carr
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D000070818:Discoidin Domain Receptors; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D020794:Receptor Protein-Tyrosine Kinases / Q000187:drug effects*; D011975:Receptors, Mitogen / Q000187:drug effects*; D015398:Signal Transduction; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001688:Biological Products; D006575:Heterocyclic Compounds, 3-Ring; D011758:Pyrroles; D011760:Pyrrolidinones; D011975:Receptors, Mitogen; C587605:discoipyrrole B; D000070818:Discoidin Domain Receptors; D020794:Receptor Protein-Tyrosine Kinases