Journal of the American Chemical Society
ARTICLE
(2) (a) Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117,
8126–8131. (b) Searle, P. A.; Molinski, T. F.; Brzezinski, L. J.; Leahy,
J. W. J. Am. Chem. Soc. 1996, 118, 9422–9423. (c) Molinski, T. F.
Tetrahedron Lett. 1996, 37, 7879–7980.
(3) Capon, R. J.; Skene, C.; Liu, E. H.; Lacey, E.; Gill, J. H.; Heilan,
K.; Friedel, T. Nat. Prod. Res. 2004, 18, 305–309.
(20) Rathke, M. W.; Sullivan, D. F. Synth. Commun. 1973, 3, 67–72.
(21) Grieco, P. A.; Cooke, R. J.; Henry, K. J.; VanderRoest, J. M.
Tetrahedron Lett. 1991, 32, 4665–4668.
(22) (a) Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, T.; Uchimoto,
K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048–6050. (b) Jin, H.;
Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644–
5646. (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc.
1977, 99, 3179–3181.
(23) Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 1295–1298.
(24) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265–268.
(25) (a) Mori, K.; Takigawa, T.; Matsuo, T. Tetrahedron 1979, 35,
933–940. (b) Hanessian, S.; Ugolini, A.; Dube, D.; Glamyan, A. Can.
J. Chem. 1984, 62, 2146–2149.
(26) Cink, R. D.; Forsyth, C. J. J. Org. Chem. 1995, 60, 8122–8123.
(27) (a) Trost, B. M.; Coppola, B. P. J. Am. Chem. Soc. 1982, 104,
6879–6881. (b) Trost, B. M.; Buch, M.; Miller, M. L. J. Org. Chem. 1988,
53, 4887–4888.
(28) (a) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969,
34, 2543–2549. (b) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973,
95, 512–519. (c) Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143–
2147.
(29) (a) Mitsunobu, O. Synthesis 1981, 1, 28. (b) Martin, S. F.;
Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017–3020.
(30) Lal, B.; Pramanik, B. N.; Manhas, M. S.; Bose, A. J. Tetrahedron
Lett. 1977, 1977–1980.
(4) (a) Forsyth, C. J.; Ahmed, F.; Cink, R. D.; Lee, C. S. J. Am. Chem.
Soc. 1998, 120, 5597–5598. (b) Evans, D. A.; Cee, V. J.; Smith, T. E.;
Fitch, D. M.; Cho, P. S. Angew. Chem., Int. Ed. 2000, 39, 2533–2536.
(c) Evans, D. A.; Fitch, D. M. Angew. Chem., Int. Ed. 2000, 39, 2536–
2540. (d) Evans, D. A.; Fitch, D. M.; Smith, T. E.; Cee, V. J. J. Am. Chem.
Soc. 2000, 122, 10033–10046. (e) Smith, A. B., III; Verhoest, P. R.;
Minbiole, K. P.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 4834–4836.
(f) Smith, A. B., III; Minbiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am.
Chem. Soc. 2001, 123, 10942–10953. (g) Gonzꢀalez, M. A.; Pattenden, G.
Angew. Chem., Int. Ed. 2003, 42, 1255–1258. (h) Pattenden, G.
Gonzꢀalez, M. A.; Little, P. B.; Millan, D. S.; Plowright, A. T.; Tornos,
J. A.; Ye, T. Org. Biomol. Chem. 2003, 1, 4173–4208. (i) Williams, D. R.;
Kiryanov, A. A.; Emde, U.; Clark, M. P.; Berliner, M. A.; Reeves, J. T.
Angew. Chem., Int. Ed. 2003, 42, 1258–1262. (j) Williams, D. R.;
Kiryanov, A. A.; Emde, U.; Clark, M. P.; Berliner, M. A.; Reeves, J. T.
Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12058–12063. (k) Li, D.; Zhang,
D.; Sun, C.; Zhang, J.; Yang, L.; Chen, J.; Liu, B.; Su, C.; Zhou, W.; Lin,
G. Chem.;Eur. J. 2006, 12, 1185–1204. (l) White, J. D.; Kuntiyong, P.;
Lee, T. H. Org. Lett. 2006, 8, 6039–6042. (m) White, J. D.; Lee, T. H.;
Kunttiyong, P. Org. Lett. 2006, 8, 6043–6046. (n) Lucas, B. S.;
Gopalsamuthiram, V.; Burke, S. D. Angew. Chem., Int. Ed. 2007, 46, 7
69–772. (o) Smith, A. B., III; Razler, T. M.; Ciavarri, J. P.; Hirose, T.;
Ishikawa, T. Org. Lett. 2005, 7, 4399–4402. (p) Smith, A. B., III; Razler,
T. M.; Ciavarri, J. P.; Hirose, T.; Ishikawa, T.; Meis, R. M. J. Org. Chem.
2008, 73, 1192–1200.
(31) Vaultier, M.; Knouzi, N.; Carrie, R. Tetrahedron Lett. 1983, 24,
763–764.
(32) Garner, P.; Yoo, J. U.; Sarabu, R.; Kennedy, V. O.; Youngs, W. J.
Tetrahedron 1998, 54, 9303–9316.
(33) Lu, Y. M.S. Thesis, University of Minnesota, 2003.
(34) Diene 45 was prepared in 87% from 3-(p-methoxylbenzyloxy)-
propanal in two steps. See Supporting Information.
(35) Paterson, I.; Goodman, J. M.; Isaka, M. Tetrahedron Lett. 1989,
30, 7121–7124.
(36) Evans, D. A.; Chapman, K. T.; Carreria, E. M. J. Am. Chem. Soc.
1988, 110, 3560–3578.
(37) Betancort, J. M.; Martin, V. S.; Padron, J. M.; Palazon, J. M.;
Ramirez, M. A.; Soler, M. A. J. Org. Chem. 1997, 62, 4584–4590.
(38) Banwell, M. G.; Bui, C. T.; Pham, H. T. T.; Simpson, G. W.
J. Chem. Soc., Perkin Trans. 1 1996, 967–969.
(5) (a) Lee, C. S. Ph.D. Thesis, University of Minnesota, 1999.
(b) Hansen, T. M. Ph.D. Thesis, University of Minnesota, 2002.
(6) Uckun, F. M.; Forsyth, C. J. Bioorg. Med. Chem. Lett. 2001, 11,
1181–1183.
(7) (a) Smith, A. B., III; Razler, T. M.; Pettit, G. R.; Chapuis, J. Org.
Lett. 2005, 7, 4403–4406. (b) Smith, A. B., III; Razler, T. M.; Meis, R. M.;
Pettit, G. R. Org. Lett. 2006, 8, 797–799. (c) Smith, A. B., III; Razler,
T. M.; Meis, R. M.; Pettit, G. R. J. Org. Chem. 2008, 73, 1201–1208 and
references therein.
(8) (a) Hansen, T. M.; Engler, M. M.; Forsyth, C. J. Bioorg. Med.
Chem. Lett. 2003, 13, 2127–2130. (b) Chen, J.; Ying, L.; Hansen, T. M.;
Engler, M. M.; Lee, C. S.; La Clair, J. J.; Forsyth, C. J. Bioorg. Med. Chem.
Lett. 2006, 16, 901–904. (c) Forsyth, C. J.; Chen, J.; Ying, L.; La Clair, J.
J. Am. Chem. Soc. 2006, 128, 3858–3859.
(39) (a) Wessel, H.-P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin
Trans. 1 1985, 2247–2250. (b) Nakajima, N.; Horita, K.; Abe, R.;
Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139–4142.
(40) (a) Huang, S. L.; Omura, K.; Swern, D. J. Org. Chem. 1976, 41,
3329–3331. (b) Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651–
1660.
(41) Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.;
Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183–
2186.
(9) (a) Crimmin, M. J.; O'Hanlon, P. J.; Rogers, N. H.; Sime, F. M.;
Walker, G. J. Chem. Soc., Perkin Trans. 1 1989, 2059.
(10) (a) Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604–3606.
(b) Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558–559.
(11) Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405–4408.
(12) (a) Cink, R. D.; Forsyth, C. J. J. Org. Chem. 1997, 62, 5672–
5673. (b) Lee, C. S.; Forsyth, C. J. Tetrahedron Lett. 1996, 37, 6449–
6452. (c) Ahmed, F.; Forsyth, C. J. Tetrahedron Lett. 1998, 39, 183–186.
(13) (a) Garner, P.; Ramakanth, S. J. Org. Chem. 1986, 51, 2609–
2612; (b) Garner, P.; Park, J. M. Org. Synth. 1998, Coll. Vol. 9, 300; 1992,
70, 18.
(42) Isher, O.; Gutmann, M.; Montavon, M.; Riiegg, R.; Ryser, G.;
Zeller, P. Helv. Chim. Acta 1957, 139, 1242–1249.
(43) (a) Schlessinger, R. H.; Pross, M. A.; Richardson, S.; Lin, P.
Tetrahedron Lett. 1985, 26, 2391–2394. (b) Trippet, S.; Walker, D. M.
J. Chem. Soc. 1961, 1266–1272.
(44) Brown, H. C.; Dhar, R. K.; Bakshi, R. K.; Pandiarajan, P. K.;
Singaram, B. J. Am. Chem. Soc. 1989, 111, 3441–3442.
(45) (a) Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett.
1982, 23, 885–888. (b) Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.;
Yonemitsu, O. Tetrahedron 1986, 42, 3021–3028.
(14) (a) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531–
1546. (b) Reetz, M. T.; Schmitz, A.; Holdgrun, X. Tetrahedron Lett.
1989, 30, 5421–5424.
(15) Cink, R. D. Ph.D. Thesis, University of Minnesota, 1998.
(16) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A.
Tetrahedron 1996, 52, 2167–2176.
(46) Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis
1994, 639–666.
(47) (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155–4156.
(b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277–7287.
(48) Evans, D. A.; Ennis, M. D.; Le, T.; Mandel, N.; Mandel, G.
J. Am. Chem. Soc. 1984, 106, 1154–1156.
(17) These results, disclosed in 1998,15 were recently replicated:
Fontana, C.; Incerti, M.; Moyna, G.; Manta, E. Tetrahedron: Asymmetry
2010, 21, 398–404.
(18) Danishefsky, S.; Kobayashi, S.; Kerwin, J. F., Jr. J. Org. Chem.
1982, 47, 1981–1983.
(49) Kim, S.-K.; Hatori, M.; Ojika, M.; Sakagami, Y.; Marumo, S.
Bioorg. Med. Chem. Lett. 1998, 6, 1975–1982.
(19) Chen, J. Ph.D. Thesis, University of Minnesota, 2004.
(50) F€urstner, A. Chem. Rev. 1999, 99, 991–1046.
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