title: Remodeling of fumagillol: discovery of an oxygen-directed oxidative Mannich reaction.
abstract: An efficient, two-step construction of highly complex alkaloid-like compounds from the natural product fumagillol is described. This approach, which mimics a biosynthetic cyclase/oxidase sequence, allows for rapid and efficient structure elaboration of the basic fumagillol scaffold with a variety of readily available coupling partners. Mechanistic experiments leading to the discovery of an oxygen-directed oxidative Mannich reaction are also described.
authors.affiliation: Center for Chemical Methodology and Library Development, Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
authors.forename: Alexander J
authors.initials: AJ
authors.lastname: Grenning
authors.forename: John K
authors.initials: JK
authors.lastname: Snyder
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D003510:Cyclohexanes; D012717:Sesquiterpenes; C057299:fumagillol; D010100:Oxygen