title: Transannular nitrone cycloaddition. A stereocontrolled entry to the spirocyclic core of pinnaic acid.
abstract: [figure: see text] Thermolysis of lactone 18 initiated a stereospecific transannular nitrone-olefin [3 + 2] cycloaddition to yield tetracycle 19. Methanolysis followed by reductive cleavage of the isoxazolidine yielded 20, representing the azaspirocyclic core of pinnaic acid (1).
authors: Department of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, USA. james.white@orst.edu
authors: J D
authors: JD
authors: White
authors: P R
authors: PR
authors: Blakemore
authors: E A
authors: EA
authors: Korf
authors: A F
authors: AF
authors: Yokochi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D009589:Nitrogen Oxides / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D009589:Nitrogen Oxides; D013141:Spiro Compounds; C015388:nitrones; C412665:pinnaic acid