Studies toward a marine toxin immunogen: enantioselective synthesis of the spirocyclic imine of (-)-gymnodimine.
[reaction: see text] An enantioselective Diels-Alder reaction catalyzed by an Evans' copper-bis(oxazoline) complex was utilized to construct a highly functionalized spirolactam, a key intermediate in our projected total synthesis of the marine toxin, gymnodimine. Additional transformations, including a mild N-tosyl group deprotection, afforded a keto spirocyclic imine moiety, the proposed pharmacophore of gymnodimine. Thus, the prepared ketone is a potentially useful intermediate for conjugation to provide an immunogen for eventual monitoring of gymnodimine and congeners.
Kong
Ke
K
Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, USA.
Moussa
Ziad
Z
Romo
Daniel
D
D018360:Crystallography, X-Ray; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D006575:Heterocyclic Compounds, 3-Ring; D006844:Hydrocarbons, Cyclic; D007097:Imines; D008387:Marine Toxins; C407350:gymnodimine