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For recent examples, see: (b) Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448.
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(d) For tandem oxacyclizations of poly(cyclic) sulfates, see: Beauchamp, T. J.; Powers, J. P.; Rychnovsky, S. D. J. Am. Chem. Soc. 1995, 117, 12873.
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0034052758
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(a) Previously reported tandem endo-oxacyclizations have been limited to low-yield formation of three six-membered rings from a 1,4,7-triepoxide: Tokiwano, T.; Fujiwara, K.; Murai, A. Synlett 2000, 335.
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(b) An earlier approach from a 1,4-diepoxide proceeded via an unexpected double inversion to afford the cis-fused bispyran: Hayashi, N.; Fujiwara, K.; Murai, A. Tetrahedron Lett. 1996, 37, 6173.
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0028913329
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endo-Regioselectivity in monooxacyclizations has been observed with antibody (ref 5a) or Co-salen catalysis (ref 5b), or more generally by placing cation-stabilizing or other directing substituents onto the epoxide (ref 5c -k). (a) Janda, K. D.; Shevlin, C. G.; Lerner, R. A. J. Am. Chem. Soc. 1995, 117, 2659.
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(e) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5335.
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(f) Adiwidjaja, G.; Flörke, H.; Kirschning, A.; Schaumann, E. Tetrahedron Lett. 1995, 36, 8771.
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(g) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158.
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(h) Oishi, T.; Maeda, K.; Hirama, M. J. Chem. Soc., Chem. Commun. 1997, 1289.
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(i) Neogi, P.; Doundoulakis, T.; Yazbak, A.; Sinha, S. C.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 11279.
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(j) Mukai, C.; Sugimoto, Y.; Ikeda, Y.; Hanaoka, M. Tetrahedron 1998, 54, 823.
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24
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0032532258
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(l) Review of oxepane synthesis: Hoberg, J. O. Tetrahedron 1998, 54, 12631.
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Hoberg, J.O.1
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25
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0000406679
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Other examples in which epoxides have been utilized as nucleophiles in oxacyclization transformations include ref 4b and (a) David, F. J. Org. Chem. 1981, 46, 3512.
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(b) Tokumasu, M.; Sasaoka, A.; Takagi, R.; Hiraga, Y.; Ohtaka, K. Chem. Commun. 1997, 875.
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(c) Alvarez, E.; Manta, E.; Martin, J. D.; Rodriguez, M. L.; Ruiz-Perez, C. Tetrahedron Lett. 1988, 29, 2093.
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(d) Alvarez, E.; Manta, E.; Martin, J. D.; Rodriguez, M. L.; Ruiz-Perez, C.; Zurita, D. Tetrahedron Lett. 1988, 29, 2097.
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29
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0000062296
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(e) Alvarez, E.; Díaz, M. T.; Pérez, R.; Ravelo, J. L.; Regueiro, A.; Vera, J. A.; Zurita, D.; Martín, J. D. J. Org. Chem. 1994, 59, 2848.
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Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
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31
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18844410382
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Shi epoxidation of the 6,7-alkene, and acetylation of the primary alcohol
-
Prepared from geraniol by a sequence of Sharpless enantioselective epoxidation of the 2,3-alkene (Gao, Y.; Klunder, J. M.; Hanson, R. M.; Masamune, H.; Ko, S. Y.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765), Shi epoxidation of the 6,7-alkene, and acetylation of the primary alcohol.
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J. Am. Chem. Soc.
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Gao, Y.1
Klunder, J.M.2
Hanson, R.M.3
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Ko, S.Y.5
Sharpless, K.B.6
-
32
-
-
85088004423
-
-
note
-
2 = 0.1129, GoF 1.168.
-
-
-
-
33
-
-
0002839259
-
-
via sequential Sharpless enantioselective epoxidation of the 2-methylene and Shi epoxidation of the remaining 5,6-alkene followed by acetylation of the primary alcohol
-
Prepared from 6-methyl-2-methylene-hept-5-en-1-ol (Takano, S.; Morimoto, M.; Satoh, S.; Ogasawara, K. Chem. Lett. 1984, 1261) via sequential Sharpless enantioselective epoxidation of the 2-methylene and Shi epoxidation of the remaining 5,6-alkene followed by acetylation of the primary alcohol.
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Chem. Lett.
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Takano, S.1
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Ogasawara, K.4
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34
-
-
85088005450
-
-
note
-
2 = 0.0929, GoF 1.123.
-
-
-
-
35
-
-
0039155654
-
-
note
-
We have not excluded the possibility of a concerted oxacyclization process rather than the stepwise mechanism shown in Figure 2.
-
-
-
-
36
-
-
0040934096
-
-
note
-
Prepared from E,E-farnesol by a three-step sequence of Sharpless enantioselective epoxidation of the 2,3-alkene, Shi epoxidation of the remaining 6,7- and 10,11-alkenes, and tert-butyl carbonate derivatization of the primary alcohol.
-
-
-
-
37
-
-
0008798085
-
-
Prepared from 6,10-dimethyl-2-methyleneundeca-5,9-dien-1-ol [(a) Ogiso, A.; Kitasawa, E.; Kurabayashi, M.; Sato, A.; Takahashi, S.; Noguchi, H.; Kuwano, H.; Kobayashi, S.; Mishima, H. Chem. Pharm. Bull. 1978, 26, 7.
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Ogiso, A.1
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Sato, A.4
Takahashi, S.5
Noguchi, H.6
Kuwano, H.7
Kobayashi, S.8
Mishima, H.9
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38
-
-
0033534422
-
-
(b) Koohang, A.; Coates, R. M.; Owen, D.; Poulter, C. D. J. Org. Chem. 1999, 64, 6.] via sequential Sharpless enantioselective epoxidation of the 2-methylene, Shi epoxidation of the remaining 5,6- and 9,10-alkenes, and tert-butyl carbonate derivatization of the primary hydroxyl.
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Koohang, A.1
Coates, R.M.2
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Poulter, C.D.4
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39
-
-
85088003768
-
-
note
-
2 = 0.0575, GoF 1.082.
-
-
-
-
40
-
-
0001418150
-
-
Morrison, J. D., Ed.; Academic Press: New York
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Reviews: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 341-409.
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Bartlett, P.A.1
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(b) Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189.
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Abe, I.1
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0027476042
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For recent examples, see: (c) Johnson, W. S.; Plummer, M. S.; Reddy, S. P.; Bartlett, W. R. J. Am. Chem. Soc. 1993, 115, 515.
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Johnson, W.S.1
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0030698069
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(d) Corey, E. J.; Luo, G., Lin, L. S. J. Am. Chem. Soc. 1997, 119, 9927.
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