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Synlett 1997; 1997(12): 1417-1419
DOI: 10.1055/s-1997-1075
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Synthetic Study on Gymnodimine: Highly Stereoselective Construction of Substituted Tetrahydrofuran and Cyclohexene Moieties

Jun Ishihara, Jun Miyakawa, Takashi Tsujimoto, Akio Murai*
  • *Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo, 060, Japan
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Publication Date:
31 December 2000 (online)

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The synthetic studies on gymnodimine, a shellfish toxin, are described. This marine toxin consists of 16-membered carbocycle, tetrahydrofuran, and spiro-imine moieties. Our synthetic strategy involves the stereoselective allylation of tetrahydrofuran compound and the exo-selective intramolecular Diels-Alder reaction.

gymnodimine - substituted tetrahydrofuran - intramolecular Diels-Alder reaction