title: Nature-inspired total synthesis of (-)-fusarisetin A.
abstract: A concise, protecting group-free total synthesis of (-)-fusarisetin A (1) was efficiently achieved in nine steps from commercially available (S)-(-)-citronellal. The synthetic approach was inspired by our proposed biosynthesis of 1. Key transformations of our strategy include a facile construction of the decalin moiety that is produced via a stereoselective IMDA reaction and a one-pot TEMPO-induced radical cyclization/aminolysis that forms the C ring of 1. Our route is amenable to analogue synthesis for biological evaluation.
authors.affiliation: Department of Chemistry and Biochemistry, University of California-San Diego , 9500 Gilman Drive, La Jolla, California 92093-0358, United States.
authors.forename: Jing
authors.initials: J
authors.lastname: Xu
authors.forename: Eduardo J E
authors.initials: EJ
authors.lastname: Caro-Diaz
authors.forename: Lynnie
authors.initials: L
authors.lastname: Trzoss
authors.forename: Emmanuel A
authors.initials: EA
authors.lastname: Theodorakis
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; C572422:fusarisetin A