(+)-Polyzonimine (1), a terpenoid insect repellent produced by a millipede, was synthesized by a reaction sequence which utilizes the asymmetric [2,3] sigmatropic rearrangement of the ammonium ylide formed from the salt (10) to generate the chiral intermediate (2).
T. Sugahara, Y. Komatsu and S. Takano, J. Chem. Soc., Chem. Commun., 1984, 214 DOI: 10.1039/C39840000214
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