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9
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0027450667
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cf. Isodunnianin: (a) Fukuyama, Y. Shida, N.; Kodama, M. Planta Med. 1993, 59, 181. Garsubellin A: (b) Fukuyama, Y.; Kuwayama, A.; Minami, H. Chem. Pharm Bull. 1997, 45, 947. Synthetic studies on garsubellin A: (c) Nicolaou K. C.; Pfefferkorn, J. A.; Kim, S.; Wei, H. X. J. Am. Chem. Soc. 1999, 121, 4724. K-252a derivatives: (d) Kaneko, M.; Saito, Y.; Saito, H.; Matsumoto, T.; Matsuda, Y.; Vaught, J. L.; Dionne, C. A.; Angeles, T. S.; Glicksman, M. A.; Neff, N. T.; Rotella, D. P.; Kauer, J. C.; Mallamo, J. P.; Hudkins, R. L. Murakata, C. J. Med. Chem. 1997, 40, 1863.
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0030918103
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cf. Isodunnianin: (a) Fukuyama, Y. Shida, N.; Kodama, M. Planta Med. 1993, 59, 181. Garsubellin A: (b) Fukuyama, Y.; Kuwayama, A.; Minami, H. Chem. Pharm Bull. 1997, 45, 947. Synthetic studies on garsubellin A: (c) Nicolaou K. C.; Pfefferkorn, J. A.; Kim, S.; Wei, H. X. J. Am. Chem. Soc. 1999, 121, 4724. K-252a derivatives: (d) Kaneko, M.; Saito, Y.; Saito, H.; Matsumoto, T.; Matsuda, Y.; Vaught, J. L.; Dionne, C. A.; Angeles, T. S.; Glicksman, M. A.; Neff, N. T.; Rotella, D. P.; Kauer, J. C.; Mallamo, J. P.; Hudkins, R. L. Murakata, C. J. Med. Chem. 1997, 40, 1863.
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0033583729
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cf. Isodunnianin: (a) Fukuyama, Y. Shida, N.; Kodama, M. Planta Med. 1993, 59, 181. Garsubellin A: (b) Fukuyama, Y.; Kuwayama, A.; Minami, H. Chem. Pharm Bull. 1997, 45, 947. Synthetic studies on garsubellin A: (c) Nicolaou K. C.; Pfefferkorn, J. A.; Kim, S.; Wei, H. X. J. Am. Chem. Soc. 1999, 121, 4724. K-252a derivatives: (d) Kaneko, M.; Saito, Y.; Saito, H.; Matsumoto, T.; Matsuda, Y.; Vaught, J. L.; Dionne, C. A.; Angeles, T. S.; Glicksman, M. A.; Neff, N. T.; Rotella, D. P.; Kauer, J. C.; Mallamo, J. P.; Hudkins, R. L. Murakata, C. J. Med. Chem. 1997, 40, 1863.
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15144358619
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cf. Isodunnianin: (a) Fukuyama, Y. Shida, N.; Kodama, M. Planta Med. 1993, 59, 181. Garsubellin A: (b) Fukuyama, Y.; Kuwayama, A.; Minami, H. Chem. Pharm Bull. 1997, 45, 947. Synthetic studies on garsubellin A: (c) Nicolaou K. C.; Pfefferkorn, J. A.; Kim, S.; Wei, H. X. J. Am. Chem. Soc. 1999, 121, 4724. K-252a derivatives: (d) Kaneko, M.; Saito, Y.; Saito, H.; Matsumoto, T.; Matsuda, Y.; Vaught, J. L.; Dionne, C. A.; Angeles, T. S.; Glicksman, M. A.; Neff, N. T.; Rotella, D. P.; Kauer, J. C.; Mallamo, J. P.; Hudkins, R. L. Murakata, C. J. Med. Chem. 1997, 40, 1863.
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Neff, N.T.10
Rotella, D.P.11
Kauer, J.C.12
Mallamo, J.P.13
Hudkins, R.L.14
Murakata, C.15
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0343350981
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matrix presented
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Compound 21 was prepared as previously reported in one step from commercially available methyl gallate; see: (a) Keserü, G. M.; Nógrádi, M.; Kajtár-Peredy, M. Liebigs Ann. Chem. 1994, 361. (b) Kuo, G.-H.; Eissenstat, M. A. Tetrahedron Lett. 1997, 38, 3343.
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Compound 21 was prepared as previously reported in one step from commercially available methyl gallate; see: (a) Keserü, G. M.; Nógrádi, M.; Kajtár-Peredy, M. Liebigs Ann. Chem. 1994, 361. (b) Kuo, G.-H.; Eissenstat, M. A. Tetrahedron Lett. 1997, 38, 3343.
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0343786648
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note
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Selective monocyanide addition to 41 could be explained as the formation of aluminum acetal iii after the reaction. (matrix presented)
-
-
-
-
50
-
-
0343350931
-
-
note
-
Further work to study the generality of this aluminum enolate epoxide opening reaction is in progress.
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52
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0026334190
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Metal-mediated reaction of ketone enolate to epoxide has been extensively studied by Crotti and associates: (a) Chini, M.; Crotti, P.; Favero, L.; Pineschi, M. Tetrahedron Lett. 1991, 32, 7583. (b) Crotti, P.; Di Bussolo, V.; Favero, L.; Pineschi, M. J. Org. Chem. 1996, 61, 9548. (c) Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 6537. (d) Crotti, P, Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M.; Napolitano E. Tetrahedron 1999, 55, 5853.
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0001435803
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Metal-mediated reaction of ketone enolate to epoxide has been extensively studied by Crotti and associates: (a) Chini, M.; Crotti, P.; Favero, L.; Pineschi, M. Tetrahedron Lett. 1991, 32, 7583. (b) Crotti, P.; Di Bussolo, V.; Favero, L.; Pineschi, M. J. Org. Chem. 1996, 61, 9548. (c) Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 6537. (d) Crotti, P, Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M.; Napolitano E. Tetrahedron 1999, 55, 5853.
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Metal-mediated reaction of ketone enolate to epoxide has been extensively studied by Crotti and associates: (a) Chini, M.; Crotti, P.; Favero, L.; Pineschi, M. Tetrahedron Lett. 1991, 32, 7583. (b) Crotti, P.; Di Bussolo, V.; Favero, L.; Pineschi, M. J. Org. Chem. 1996, 61, 9548. (c) Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 6537. (d) Crotti, P, Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M.; Napolitano E. Tetrahedron 1999, 55, 5853.
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55
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0033617237
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Metal-mediated reaction of ketone enolate to epoxide has been extensively studied by Crotti and associates: (a) Chini, M.; Crotti, P.; Favero, L.; Pineschi, M. Tetrahedron Lett. 1991, 32, 7583. (b) Crotti, P.; Di Bussolo, V.; Favero, L.; Pineschi, M. J. Org. Chem. 1996, 61, 9548. (c) Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 6537. (d) Crotti, P, Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M.; Napolitano E. Tetrahedron 1999, 55, 5853.
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For representative examples of aluminum ester enolate addition to epoxide, see: (a) Danishefsky, S.; Kitahara, T.; Tsai, M.; Dynak, J. J. Org. Chem. 1976, 41, 1669. (b) Taylor, S. K.; Fried, J. A.; Grassl, Y. N.; Marolewski, A. E.; Pelton, E. A.; Poel, T.-J.; Rezanka, D. S.; Whittaker, M. R. J. Org. Chem. 1993, 58, 7304.
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0001215705
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For representative examples of aluminum ester enolate addition to epoxide, see: (a) Danishefsky, S.; Kitahara, T.; Tsai, M.; Dynak, J. J. Org. Chem. 1976, 41, 1669. (b) Taylor, S. K.; Fried, J. A.; Grassl, Y. N.; Marolewski, A. E.; Pelton, E. A.; Poel, T.-J.; Rezanka, D. S.; Whittaker, M. R. J. Org. Chem. 1993, 58, 7304.
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58
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0343786647
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Compound 45 was synthesized in three steps from commercially available sesamol: (a) Alexander, B. H.; Gertler, S. I.; Brown, R. T.; Oda, T. A.; Beroza, M. J. Org. Chem. 1959, 4, 49. (b) Schuda, P. F.; Price, W. A. J. Org. Chem. 1987, 52, 1972.
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59
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0001597307
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Compound 45 was synthesized in three steps from commercially available sesamol: (a) Alexander, B. H.; Gertler, S. I.; Brown, R. T.; Oda, T. A.; Beroza, M. J. Org. Chem. 1959, 4, 49. (b) Schuda, P. F.; Price, W. A. J. Org. Chem. 1987, 52, 1972.
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