Radical cyclisation with high diastereofacial selectivity: asymmetric synthesis of (+)-12b-epidevinylantirhine

Abstract

Radical cyclisation of the chiral α,β-unsaturated ester 1, carried out in the presence of MAD, gives six-membered cyclic acetal 2 diastereoselectively, which is transformed into (+)-12b-epidevinylantirhine 7.

References

1. B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon, Oxford, 1986; D. P. Curran, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and M. F. Semmelhack, Pergamon, Oxford, 1991, vol. 4, p. 715; A. L. J. Beckwith, Chem. Soc. Rev., 1993, 143; G. Stork and N. H. Baine, J. Am. Chem. Soc., 1982, 104, 2321.
2. M. Ihara, K. Yasui, N. Taniguchi and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1990, 1469.
3. (a) E. Wenkert, M. Guo, M. J. Pestchanker, Y.-J. Shi and Y. D. Vankar, J. Org. Chem., 1989, 54, 1166; (b) M. Lounasmaa, R. Jokela, M. Halonen and J. Miettinen, Heterocycles, 1993, 36, 2523.
4. B. M. Trost and T. R. Verhoeven, J. Am. Chem. Soc., 1980, 102, 4743.
5. W. R. Roush, H. R. Gillis and A. I. Ko, J. Am. Chem. Soc., 1982, 104, 2269.
6. Y. Ueno, K. Chino, M. Watanabe, O. Moriya and M. Okawara, J. Am. Chem. Soc., 1982, 104, 5564.
7. K. Nozaki, K. Oshima and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 2547.
8. M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida and N. Kawahara, J. Am. Chem. Soc., 1994, 116, 6455.
9. K. Maruoka, T. Itoh, M. Sakurai, K. Nonoshita and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 3588.
10. P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon, Oxford, 1983.
11. G. Toth, O. Clauder, K. Gesztes, S. S. Yemul and G. Snatzke, J. Chem. Soc., Perkin Trans. 2, 1980, 701.