Studies toward (-)-gymnodimine: concise routes to the spirocyclic and tetrahydrofuran moieties.
[formula: see text] (-)-Gymnodimine is a member of a unique class of potent marine toxins possessing imines within a spirocylic array. Herein we report the synthesis of the tetrahydrofuran fragment and a strategy toward the spirocyclic imine fragment of this family of toxins. Key reactions include an asymmetric anti-aldol reaction to set the stereochemistry of the tetrahydrofuran and a formal, intermolecular Diels-Alder reaction involving an alpha-methylene-delta-lactam and a dienyne.
Yang
J
J
Department of Chemistry, Texas A&M University, College Station 77843-3012, USA.
Cohn
S T
ST
Romo
D
D
D005663:Furans; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D006844:Hydrocarbons, Cyclic; D007097:Imines; D007202:Indicators and Reagents; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D005663:Furans; D006575:Heterocyclic Compounds, 3-Ring; D006844:Hydrocarbons, Cyclic; D007097:Imines; D007202:Indicators and Reagents; D008387:Marine Toxins; C407350:gymnodimine