CAN induced double ether ring formation: synthesis of trans- and cis-fused tricyclic ethers from 3-oxabicyclo[3.1.0]hexyl sulfides

Abstract

CAN oxidation of 3-oxabicyclo[3.1.0]hexy sulfides 4 and 5 possessing two hydroxy groups in the C-2 and C-4 side chains promoted a double ether ring formation along with a cleavage of the most substituted cyclopropyl bond to give tricyclic ketal adducts 8 and 10, which were converted to trans- and cis-fused tricyclic ethers 9 and 11 with high or moderate stereoselectivity by a TMSOTf-mediated trialkylsilane reduction.

References

1. Review: E. Alvarez, M. Candenas, R. Pérez, J. L. Ravelo and J. D. Martín, Chem. Rev., 1995, 95, 1953 and references cited therein N. Hiro, H. Matsukura, G. Matsuo and T. Nakata, Tetrahedron Lett., 1999, 40, 2811; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337; K. Fujiwara, K. Saka, D. Takaoka and A. Murai, Synlett, 1999, 1037; J. L. Bowman and F. E. McDonald, J. Org. Chem., 1998, 63, 3680; T. Oishi, Y. Nagumo and M. Hirama, Chem. Commun., 1998, 1041; J. S. Clark and J. G. Kettle, Tetrahedron Lett., 1997, 38, 123; K. C. Nicolaou, M. H. D. Postema and C. F. Claiborne, J. Am. Chem. Soc., 1996, 118, 1565; S. D. Rychnovsky and V. H. Dahanukar, J. Org. Chem., 1996, 61, 7648; M. Isobe, S. Hosokawa and K. Kira, Chem. Lett., 1996, 473; I. Kadota, P. Jung-Youl, N. Koumura, G. Pollaud, Y. Matsukawa and Y. Yamamoto, Tetrahedron Lett., 1995, 36, 5777.
2. Y. Mori, K. Yaegashi and H. Furukawa, Tetrahedron Lett., 1999, 40, 7239; P. A. Evans, J. D. Roseman and L. T. Garber, J. Org. Chem., 1996, 61, 4880; N. Hayashi, K. Fujisawa and A. Murai, Tetrahedron Lett., 1996, 37, 6173; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. de Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869.
3. Y. Takemoto, T. Ibuka, H. Hayase, A. Iwanaga, S. Yamagata, C. Iwata and T. Tanaka, Tetrahedron Lett., 1998, 39, 7545; Y. Takemoto, T. Ohra, H. Koike, S. Furuse, C. Iwata and H. Ohishi, J. Org. Chem., 1994, 59, 4727; Y. Takemoto, T. Ohra, S. Furuse, H. Koike and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1529.
4. K. C. Nicolaou, C.-K. Hwang and D. A. Nugiel, J. Am. Chem. Soc., 1989, 111, 4136; R. Noyori, S. Murata and M. Suzuki, Tetrahedron, 1981, 37, 3899.
5. An authentic sample of 11B was described in the following paper: E. Alvarez, R. Pérez, M. Rico, R. M. Rodríguez and D. Martín, J. Org. Chem., 1996, 61, 3003.