Angewandte
Chemie
[8] K.-H. Son, J.-Y. Kwon, H.-W. Jeong, H.-K. Kim, C.-J. Kim, Y.-H.
Chang, J.-D. Choi, B.-M. Kwon, Bioorg. Med. Chem. 2002, 10,
185.
[9] H. Hatanaka, T. Kino, M. Hashimoto, Y. Tsurumi, A. Kuroda, H.
Tanaka, T. Goto, M. Okuhara, J. Antibiot. 1988, 41, 999.
[10] a) G. Zhou, C. W. Tsai, J. O. Liu, J. Med. Chem. 2003, 46, 3452;
b) V. Rodeschini, J.-G. Boiteau, P. V. de Weghe, C. Tarnus, J.
Eustache, J. Org. Chem. 2004, 69, 357; c) R. Maztischek, A.
Huwe, A. Giannis, Org. Biomol. Chem. 2005, 3, 2150, and
references therein.
[11] a) E. J. Corey, B. B. Snider, J. Am. Chem. Soc. 1972, 94, 2549;
b) E. J. Corey, J. P. Dittami, J. Am. Chem. Soc. 1985, 107, 256;
c) D. A. Vosburg, S. Weiler, E. J. Sorensen, Angew. Chem. 1999,
111, 1022; Angew. Chem. Int. Ed. 1999, 38, 971; d) M. Hutchings,
D. Moffat, N. S. Simpkins, Synlett 2001, 661.
Fꢂrstner, K. Grela, C. Mathes, C. W. Lehmann, J. Am. Chem.
Soc. 2000, 122, 11799.
[27] Vinyl bromide 14 was prepared by Sorensenꢀs modified
route[11c,18] of a synthetic procedure originally reported by
Corey et al.; see: E. J. Corey, J. Lee, B. E. Roberts, Tetrahedron
Lett. 1997, 38, 8915.
[28] G. M. Rubottom, M. A. Vazquez, D. R. Pellagrina, Tetrahedron
Lett. 1974, 4319.
[29] When the spiro epoxide is formed first, the diastereoselectivity
of the epoxidation of the side chain is not high. See also
reference [11c].
[30] a) D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155; b) D. B.
Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277; c) R. E.
Ireland, L. Liu, J. Org. Chem. 1993, 58, 2899.
[31] Epoxidation of the side chain was performed as the last step of
Coreyꢀs synthesis;[11b] however, we thought it was better to
oxidize much earlier owing to the instability of the precursor.
[32] D. R. Pesiri, D. K. Morita, T. Walker, W. Tumas, Organometallics
1990, 18, 4916.
[33] T. W. Greene, P. G. M. Wuts, Protective Groups in Organic
Synthesis, 3rd ed., Wiley, New York, 1999.
[34] The stereochemistry of 28 and 29 was not determined.
[35] D. E. Cane, R. H. Levin, J. Am. Chem. Soc. 1975, 97, 1282.
[12] A. Barco, S. Benetti, C. D. Risi, P. Marchetti, G. P. Pollini, V.
Zanirato, Tetrahedron: Asymmetry 1998, 9, 2857.
[13] a) S. Bath, D. C. Billington, S. D. Gero, B. Quiclet-Sire, M.
Samadi, J. Chem. Soc. Chem. Commun. 1994, 1495; b) D. H. R.
Barton, S. Bath, D. C. Billington, S. D. Gero, B. Quiclet-Sire, M.
Samadi, J. Chem. Soc. Perkin Trans. 1 1995, 1551.
[14] D. F. Taber, T. E. Christos, A. L. Rheingold, I. A. Guzei, J. Am.
Chem. Soc. 1999, 121, 5589.
[15] D. Kim, S. K. Ahn, H. Bae, W. J. Choi, H. S. Kim, Tetrahedron
Lett. 1997, 38, 4437.
[16] O. Bedel, A. Haudrechy, Y. Langlois, Eur. J. Org. Chem. 2004,
3813.
[17] a) S. Amano, N. Ogawa, M. Ohtsuka, S. Ogawa, N. Chida, Chem.
Commun. 1998, 1263; b) S. Amano, N. Ogawa, M. Ohtsuka, N.
Chida, Tetrahedron 1999, 55, 2205.
[18] D. A. Vosburg, S. Weiler, E. J. Sorensen, Chirality 2003, 15, 156.
[19] J.-G. Boiteau, P. Van de Weghe, J. Eustache, Org. Lett. 2001, 3,
2737.
[20] E. J. Corey, A. Guzman-Perez, M. C. Noe, J. Am. Chem. Soc.
1994, 116, 12109.
[21] a) Y. Hayashi, J. Yamaguchi, K. Hibino, M. Shoji, Tetrahedron
Lett. 2003, 44, 8293; b) Y. Hayashi, J. Yamaguchi, T. Sumiya, M.
Shoji, Angew. Chem. 2004, 116, 1132; Angew. Chem. Int. Ed.
2004, 43, 1112; c) Y. Hayashi, J. Yamaguchi, T. Sumiya, K.
Hibino, M. Shoji, J. Org. Chem. 2004, 69, 5966; d) Y. Hayashi, J.
Yamaguchi, K. Hibino, T. Sumiya, T. Urushima, M. Shoji, D.
Hashizume, H. Koshino, Adv. Synth. Catal. 2004, 346, 1435; e) G.
Zhong, Angew. Chem. 2003, 115, 4379; Angew. Chem. Int. Ed.
2003, 42, 4247; f) S. P. Brown, M. P. Brochu, C. J. Sinz, D. W. C.
MacMillan, J. Am. Chem. Soc. 2003, 125, 10808; g) A. Bøgevig,
H. Sundeen, A. Cꢁrdova, Angew. Chem. 2004, 116, 1129; Angew.
Chem. Int. Ed. 2004, 43, 1109; h) A. Cꢁrdova, H. Sunden, A.
Bøgevig, M. Johansson, F. Himo, Chem. Eur. J. 2004, 10, 3673;
i) N. Momiyama, H. Torii, S. Saito, H. Yamamoto, Proc. Natl.
Acad. Sci. USA 2004, 101, 5374; j) W. Wang, J. Wang, H. Li, L.
Liao, Tetrahedron Lett. 2004, 45, 7235; k) H. Sunden, N. Dahlin,
I. Ibrahem, H. Adolfsson, A. Cꢁrdova, Tetrahedron Lett. 2005,
46, 3385; for a review, see: l) P. Merino, T. Tejero, Angew. Chem.
2004, 116, 3055; Angew. Chem. Int. Ed. 2004, 43, 2995.
[22] E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1965, 87, 1353.
[23] K. B. Sharpless, R. C. Michaelson, J. Am. Chem. Soc. 1973, 95,
6136.
[24] S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 537.
[25] For hydroxy-directed Michael reaction, see: a) K. A. Swiss, D. C.
Liotta, C. A. Maryanoff, J. Am. Chem. Soc. 1990, 112, 9393;
b) K. A. Swiss, W. Hinkley, C. A. Maryanoff, D. C. Liotta,
Synthesis 1992, 127; c) M. Solomon, W. C. L. Jamison, M.
MaCormick, D. Liotta, D. A. Cherry, J. E. Mills, R. D. Shah,
J. D. Rodgers, C. A. Maryanoff, J. Am. Chem. Soc. 1988, 110,
3702.
[26] For Michael reactions of zincate, see: a) M. Suzuki, Y. Morita, H.
Koyano, M. Koga, R. Noyori, Tetrahedron 1990, 46, 4809; b) A.
Angew. Chem. Int. Ed. 2006, 45, 789 –793
ꢀ 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
793