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Paper | Regular issue | Vol 45, No. 1, 1997, pp.147-156
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7655
INOC Reaction in Alkaloid Synthesis — Stereocontrolled Formal Total Synthesis of (+)-Pumiliotoxin C

Masahiro Toyota,* Takanobu Asoh, and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


A formal total synthesis of (+)-pumiliotoxin C (1), the antipode of the arrow poison frog toxin, starting from the chirally homogeneous (1’S, 6’S)-2-(6’-benzyloxymethyl-2’-cyclohexyl)ethanol (2) is described. The synthesis features the intramolecular nitrile oxide cycloaddition (INOC) reaction of the nitro olefin (5) to furnish the isoxazoline (6).