The total synthesis of the natural (±)-cuparene (1) and (±)-herbertene (2) has been carried out in eight steps from 2-cyclohexen-1-one (3) via a key quaternary carbon centre construction using a SmI2-promoted rearrangement of 2,3-epoxy alcohol.
(a) MatsuoA., YukiS., and NakayamaM., J. Chem. Soc., Perkin Trans. 1., 1986, 701; (b) Y. Fukuyama and Y. Asakawa, J. Chem. Soc., Perkin Trans. 1., 1991, 2737; (c) Y. Fukuyama, Y. Kiriyama and M. Kodamn, Tetrahedron Lett., 1996, 37, 1261.
2.
(a) FukuyamaY., YuasaH., TonoiY., HaradaK., WadaM., AsakawaY., and HashimotoT., Tetrahedron, 2001, 57, 9299; (b) Takano, S.; Moriya, M.; Ogasawara, K. Tetrahedron Lett. 1992, 33, 329; (c) T.–L. Ho and M.–H. Chang, J. Chem. Soc., Perkin Trans. 1., 1999, 2479; (d) F. G. Favaloro, C. A. Goudreau, B. P. Mundy, T. Poon, S. V. Slobodzian and B. L. Jensen, Syn. Commun., 2001, 31, 1847.
3.
MaruokaK., OoiT., and YamamotoH., J. Am. Chem. Soc., 1989, 111, 6431.
4.
BirdC.W., YeongY. C., and HudecJ., Synthesis, 1974, 27.
