title: Total Synthesis of the Antitumor Antibiotic Basidalin.
abstract: The first synthesis of the tetronamide antibiotic basidalin was accomplished in five steps and 39% overall yield from readily available 4-bromo-2-triisopropylsilyloxyfuran and 2-formyl-1,3-dithiane. Highlights include: (i) regio- and stereocontrolled assemblage of a pivotal (Z)-γ-ylidene-β-bromobutenolide intermediate by stereodirected vinylogous aldol condensation (SVAC), (ii) installation of the amino group via aza-Michael addition/elimination, and crucially (iii) facile access to basidalin by late-stage dithiane removal.
authors.affiliation: Department of Chemistry, Pavillon Alexandre-Vachon, Université Laval , 1045 Avenue de la Médecine, Quebec City, Quebec G1V 0A6, Canada.
authors.forename: Jaime A M
authors.initials: JA
authors.lastname: Acosta
authors.affiliation: Department of Chemistry, Pavillon Alexandre-Vachon, Université Laval , 1045 Avenue de la Médecine, Quebec City, Quebec G1V 0A6, Canada.
authors.forename: Ramesh
authors.initials: R
authors.lastname: Muddala
authors.affiliation: Department of Chemistry, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais (UFMG) , Av. Pres. Antônio Carlos, 6627, Campus Pampulha, Belo Horizonte, 31270-901, MG, Brazil.
authors.forename: Luiz C A
authors.initials: LC
authors.lastname: Barbosa
authors.affiliation: Department of Chemistry, Pavillon Alexandre-Vachon, Université Laval , 1045 Avenue de la Médecine, Quebec City, Quebec G1V 0A6, Canada.
authors.forename: John
authors.initials: J
authors.lastname: Boukouvalas
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D061065:Polyketides / Q000737:chemistry*; D011807:Quinolizines / Q000737:chemistry; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000903:Antibiotics, Antineoplastic; D005663:Furans; D061065:Polyketides; D011807:Quinolizines; D013457:Sulfur Compounds; C438055:dithiane; C585986:hippolachnin A; C038319:basidalin; C116609:3-hydroxybutanal