title: Total synthesis of (-)-fusarisetin A and reassignment of the absolute configuration of its natural counterpart.
abstract: The first total synthesis of (-)-fusarisetin A, the enantiomer of naturally occurring acinar morphogenesis inhibitor (+)-fusarisetin A, was accomplished in 13 steps, leading to the reassignment of the absolute configuration of the natural product. The synthesis featured a Lewis acid-promoted intramolecular Diels-Alder reaction, a Pd-catalyzed O→C allylic rearrangement, a chemoselective Wacker oxidation, and a Dieckmann condensation/hemiketalization cascade.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Deng
authors.forename: Bo
authors.initials: B
authors.lastname: Zhu
authors.forename: Zhaoyong
authors.initials: Z
authors.lastname: Lu
authors.forename: Haixin
authors.initials: H
authors.lastname: Yu
authors.forename: Ang
authors.initials: A
authors.lastname: Li
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002384:Catalysis; D005670:Fusarium / Q000737:chemistry / Q000378:metabolism*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D010165:Palladium
chemical_list: D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; C572422:fusarisetin A; D010165:Palladium