title: Concise total synthesis of (-)-auxofuran by a click Diels-Alder strategy.
abstract: The first synthesis of auxofuran, a newly discovered auxin-like signaling molecule of streptomycetes, has been achieved in seven steps and 59% overall yield from commercial starting materials. Central to the synthetic route is a click-unclick Diels-Alder cycloaddition/cycloreversion regimen enabling rapid access to an advanced intermediate from an unactivated alkyne.
authors.affiliation: Département de Chimie, Pavillon Alexandre-Vachon, Université Laval , 1045 Avenue de la Médecine, Quebec City, Quebec G1 V 0A6, Canada.
authors.forename: John
authors.initials: J
authors.lastname: Boukouvalas
authors.forename: Richard P
authors.initials: RP
authors.lastname: Loach
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D000480:Alkynes; D001572:Benzofurans; C518211:auxofuran