Studies on the synthesis of gymnodimine. construction of the spiroimine portion via Diels-Alder cycloaddition.
An azaspiro[5.5]undecadiene corresponding to a subunit of the shellfish toxin gymnodimine was synthesized by Diels-Alder cycloaddition. One member of the pair of stereoisomeric adducts was transformed to a spiroimine, which will serve as the core around which the macrocyclic portion of the toxin will be assembled. [structure: see text]
White
James D
JD
Department of Chemistry, Oregon State University, Corvallis, OR 97331-4003, USA. james.white@orst.edu
Wang
Guoqiang
G
Quaranta
Laura
L
D000818:Animals; D018360:Crystallography, X-Ray; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D010125:Ostreidae / Q000737:chemistry
D006575:Heterocyclic Compounds, 3-Ring; D006844:Hydrocarbons, Cyclic; D007097:Imines; D007202:Indicators and Reagents; D008387:Marine Toxins; C407350:gymnodimine