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(s) Iwama, S.; Gao, W. G.; Shinada, T.; Ohfune, Y. Synlett 2000, 1631; (t) Panek, J.
S.; Masse, C. E. Angew. Chem., Int. Ed. 1999, 38, 1093; (u) Kang, S. H.; Jun, H. S.;
Youn, J. H. Synlett 1998, 1045; (v) Corey, E. J.; Li, W. D.; Reichard, G. A. J. Am.
Chem. Soc. 1998, 120, 2330; (w) Corey, E. J.; Li, W. D.; Nagamitsu, T. Angew.
Chem., Int. Ed. 1998, 37, 1676; (x) Chida, N.; Takeoka, J.; Ando, K.; Tsutsumi, N.;
Ogawa, S. Tetrahedron 1997, 53, 16287; (y) Nagamitsu, T.; Sunazuka, T.; Tanaka,
H.; Omura, S.; Sprengeler, P. A.; Smith, A. B. J. Am. Chem. Soc. 1996, 118, 3584; (z)
Chida, N.; Takeoka, J.; Tsutsumi, N.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1995,
793; (aa) Uno, H.; Baldwin, J. E.; Russell, A. T. J. Am. Chem. Soc. 1994, 116, 2139;
(ab) Sunazuka, T.; Nagamitsu, T.; Matsuzaki, K.; Tanaka, H.; Omura, S.; Smith, A.
B. J. Am. Chem. Soc. 1993, 115, 5302; (ac) Corey, E. J.; Reichard, G. A.; Kania, R.
Tetrahedron Lett. 1993, 34, 6977; (ad) Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc.
1992, 114, 10677.
Supplementary data
Supplementary data (experimental procedures and character-
ization data) associated with this article can be found, in the online
References and notes
1. Õmura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.;
Sasaki, Y. J. Antibiot. 1991, 44, 113.
2. Fenteany, G.; Standaert, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L.
Science 1995, 268, 726.
4. (a) Vaswani, R. G.; Chamberlin, A. R. J. Org. Chem. 2008, 73, 1661; (b) Vaswani, R.
G.; Limon, A.; Reyes-Ruiz, J. M.; Miledi, R.; Chamberlin, A. R. Bioorg. Med. Chem.
Lett. 2009, 19, 132.
3. (a) Gu, W.; Silverman, R. B. J. Org. Chem. 2011, 76, 8287; (b) Hameed, A.; Blake, A.
J.; Hayes, C. J. Synlett 2010, 535; (c) Hayes, C. J.; Sherlock, A. E.; Green, M. P.;
Wilson, C.; Blake, A. J.; Selby, M. D.; Prodger, J. C. J. Org. Chem. 2008, 73, 2041; (d)
Pattenden, G.; Rescourio, G. Org. Biomol. Chem. 2008, 6, 3428; (e) Miyaoka, H.;
Yamanishi, M.; Hoshino, A.; Mitome, H.; Kawashima, E. Chem. Pharm. Bull. 2008,
56, 738; (f) Legeay, J.-C.; Langlois, N. J. Org. Chem. 2007, 72, 10108; (g) Yoon, C.
H.; Flanigan, D. L.; Yoo, K. S.; Jung, K. W. Eur. J. Org. Chem. 2007, 37; (h) Gilley, C.
B.; Buller, M. J.; Kobayashi, Y. Org. Lett. 2007, 9, 3631; (i) Shibasaki, M.; Kanai, M.;
Fukuda, N. Chem. Asian J. 2007, 2, 20; (j) Fukuda, N.; Sasaki, K.; Sastry, T. V. R. S.;
Kanai, M.; Shibasaki, M. J. Org. Chem. 2006, 7, 4165; (k) Hayes, C. J.; Sherlock, A.
E.; Selby, M. D. Org. Biomol. Chem. 2006, 4, 193; (l) Balskus, E. P.; Jacobsen, E. N. J.
Am. Chem. Soc. 2006, 128, 6810; (m) Wardrop, D. J.; Bowen, E. G. Chem. Commun.
2005, 5106; (n) Donohoe, T. J.; Sintim, H. O.; Sisangia, L.; Ace, K. W.; Guyo, P. M.;
Cowley, A.; Harling, J. D. Chem. Eur. J. 2005, 11, 4227; (o) Donohoe, T. J.; Sintim,
H. O.; Sisangia, L.; Harling, J. D. Angew. Chem., Int. Ed. 2004, 43, 2293; (p) Ooi, H.;
Ishibashi, N.; Iwabuchi, Y.; Ishihara, J.; Hatekeyama, S. J. Org. Chem. 2004, 69,
7765; (q) Brennan, C. J.; Pattenden, G.; Rescourio, G. Tetrahedron Lett. 2003, 44,
8757; (r) Green, M. P.; Prodger, J. C.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 6609;
5. (a) Honda, T.; Hisa, C. Heterocycles 2010, 80, 1381; (b) Filosa, R.; Holder, C.;
Auberson, Y. P. Tetrahedron Lett. 2006, 47, 8929; (c) Tamura, O.; Yanagimachi, T.;
Ishibashi, H. Tetrahedron: Asymmetry 2003, 14, 3033; (d) Nagumo, S.; Matoba, A.;
Ishii, Y.; Yamaguchi, S.; Akutsu, N.; Nishijima, H.; Nishida, A.; Kawahara, N.
Tetrahedron 2002, 58, 9871; (e) Cossy, J.; Mirguet, O.; Gomez Pardo, D. Synlett
2001, 1575; (f) Nagumo, S.; Mizukami, M.; Akutsu, N.; Nishida, A.; Kawahara, N.
Tetrahedron Lett. 1999, 40, 3209; (g) Sato, T.; Kugo, Y.; Nakaumi, E.; Ishibashi, H.;
Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1995, 1801.
6. The preparation of these compounds is described in full in the electronic
Supplementary data associated with this Letter.
7. Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706.
8. See conversion of compound SI-66 into compound 2 in the Supplementary data
of the following Letter: Brichacek, M.; Lee, D.; Njardarson, J. T. Org. Lett. 2008, 10,
5023.
9. Oba, M.; Ito, C.; Hayashi, T.; Nishiyama, K. Tetrahedron Lett. 2009, 50, 5053.