메뉴 건너뛰기




Volumn 119, Issue 50, 1997, Pages 12150-12158

Stereospecific formation of optically active 5-alkyl-4-methyl-3- [(trialkylsilyl)oxy]-2-([(trialkylsilyl)oxy]methyl)tetrahydrofurans via diastereoselective epoxidation and rearrangement of 5-[(trialkylsilyl)oxy]- 2-alken-1-ols

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; IONOPHORE; TETRAHYDROFURAN DERIVATIVE;

EID: 0031576703     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972507o     Document Type: Article
Times cited : (55)

References (34)
  • 13
    • 15844366864 scopus 로고
    • For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Burns, C. J. Contemp. Org. Syn. 1995, 2.3, 189-207. For some recent examples, see: (c) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148. (d) O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. (e) Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Lett. 1994, 35, 4183. (f) Angle, S. R.; Wei, G. P.; Ko, Y. K.; Kubo, K. J. Am. Chem. Soc. 1995, 117, 8041. (g) Gurjar, M. K.; Mainkar, P. S. Heterocycles 1990, 31, 407. (h) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149. (i) Bonnaffé, D.; Simon, H. Tetrahedron 1992, 49, 9695. (j) Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339.
    • (1987) Tetrahedron , vol.43 , pp. 3309
    • Boivin, T.L.B.1
  • 14
    • 2642678267 scopus 로고
    • 2.3
    • For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Burns, C. J. Contemp. Org. Syn. 1995, 2.3, 189-207. For some recent examples, see: (c) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148. (d) O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. (e) Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Lett. 1994, 35, 4183. (f) Angle, S. R.; Wei, G. P.; Ko, Y. K.; Kubo, K. J. Am. Chem. Soc. 1995, 117, 8041. (g) Gurjar, M. K.; Mainkar, P. S. Heterocycles 1990, 31, 407. (h) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149. (i) Bonnaffé, D.; Simon, H. Tetrahedron 1992, 49, 9695. (j) Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339.
    • (1995) Contemp. Org. Syn. , pp. 189-207
    • Burns, C.J.1
  • 15
    • 0028051951 scopus 로고
    • For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Burns, C. J. Contemp. Org. Syn. 1995, 2.3, 189-207. For some recent examples, see: (c) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148. (d) O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. (e) Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Lett. 1994, 35, 4183. (f) Angle, S. R.; Wei, G. P.; Ko, Y. K.; Kubo, K. J. Am. Chem. Soc. 1995, 117, 8041. (g) Gurjar, M. K.; Mainkar, P. S. Heterocycles 1990, 31, 407. (h) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149. (i) Bonnaffé, D.; Simon, H. Tetrahedron 1992, 49, 9695. (j) Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339.
    • (1994) J. Org. Chem. , vol.59 , pp. 7148
    • Molander, G.A.1    Swallow, S.2
  • 16
    • 0028104844 scopus 로고
    • For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Burns, C. J. Contemp. Org. Syn. 1995, 2.3, 189-207. For some recent examples, see: (c) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148. (d) O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. (e) Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Lett. 1994, 35, 4183. (f) Angle, S. R.; Wei, G. P.; Ko, Y. K.; Kubo, K. J. Am. Chem. Soc. 1995, 117, 8041. (g) Gurjar, M. K.; Mainkar, P. S. Heterocycles 1990, 31, 407. (h) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149. (i) Bonnaffé, D.; Simon, H. Tetrahedron 1992, 49, 9695. (j) Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339.
    • (1994) J. Org. Chem. , vol.59 , pp. 6629
    • O'Leary, D.J.1    Kishi, Y.2
  • 17
    • 0028238636 scopus 로고
    • For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Burns, C. J. Contemp. Org. Syn. 1995, 2.3, 189-207. For some recent examples, see: (c) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148. (d) O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. (e) Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Lett. 1994, 35, 4183. (f) Angle, S. R.; Wei, G. P.; Ko, Y. K.; Kubo, K. J. Am. Chem. Soc. 1995, 117, 8041. (g) Gurjar, M. K.; Mainkar, P. S. Heterocycles 1990, 31, 407. (h) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149. (i) Bonnaffé, D.; Simon, H. Tetrahedron 1992, 49, 9695. (j) Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4183
    • Zhao, Y.1    Beddoes, R.L.2    Quayle, P.3
  • 18
    • 0029092475 scopus 로고
    • For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Burns, C. J. Contemp. Org. Syn. 1995, 2.3, 189-207. For some recent examples, see: (c) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148. (d) O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. (e) Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Lett. 1994, 35, 4183. (f) Angle, S. R.; Wei, G. P.; Ko, Y. K.; Kubo, K. J. Am. Chem. Soc. 1995, 117, 8041. (g) Gurjar, M. K.; Mainkar, P. S. Heterocycles 1990, 31, 407. (h) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149. (i) Bonnaffé, D.; Simon, H. Tetrahedron 1992, 49, 9695. (j) Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 8041
    • Angle, S.R.1    Wei, G.P.2    Ko, Y.K.3    Kubo, K.4
  • 19
    • 0002187380 scopus 로고
    • For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Burns, C. J. Contemp. Org. Syn. 1995, 2.3, 189-207. For some recent examples, see: (c) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148. (d) O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. (e) Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Lett. 1994, 35, 4183. (f) Angle, S. R.; Wei, G. P.; Ko, Y. K.; Kubo, K. J. Am. Chem. Soc. 1995, 117, 8041. (g) Gurjar, M. K.; Mainkar, P. S. Heterocycles 1990, 31, 407. (h) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149. (i) Bonnaffé, D.; Simon, H. Tetrahedron 1992, 49, 9695. (j) Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339.
    • (1990) Heterocycles , vol.31 , pp. 407
    • Gurjar, M.K.1    Mainkar, P.S.2
  • 20
    • 0001408368 scopus 로고
    • For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Burns, C. J. Contemp. Org. Syn. 1995, 2.3, 189-207. For some recent examples, see: (c) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148. (d) O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. (e) Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Lett. 1994, 35, 4183. (f) Angle, S. R.; Wei, G. P.; Ko, Y. K.; Kubo, K. J. Am. Chem. Soc. 1995, 117, 8041. (g) Gurjar, M. K.; Mainkar, P. S. Heterocycles 1990, 31, 407. (h) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149. (i) Bonnaffé, D.; Simon, H. Tetrahedron 1992, 49, 9695. (j) Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 3149
    • Tonn, C.E.1    Palazón, J.M.2    Ruiz-Pérez, C.3    Rodríguez, M.L.4    Martín, V.S.5
  • 21
    • 0026496904 scopus 로고
    • For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Burns, C. J. Contemp. Org. Syn. 1995, 2.3, 189-207. For some recent examples, see: (c) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148. (d) O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. (e) Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Lett. 1994, 35, 4183. (f) Angle, S. R.; Wei, G. P.; Ko, Y. K.; Kubo, K. J. Am. Chem. Soc. 1995, 117, 8041. (g) Gurjar, M. K.; Mainkar, P. S. Heterocycles 1990, 31, 407. (h) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149. (i) Bonnaffé, D.; Simon, H. Tetrahedron 1992, 49, 9695. (j) Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339.
    • (1992) Tetrahedron , vol.49 , pp. 9695
    • Bonnaffé, D.1    Simon, H.2
  • 22
    • 0031585115 scopus 로고    scopus 로고
    • For reviews, see: (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (b) Burns, C. J. Contemp. Org. Syn. 1995, 2.3, 189-207. For some recent examples, see: (c) Molander, G. A.; Swallow, S. J. Org. Chem. 1994, 59, 7148. (d) O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. (e) Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Lett. 1994, 35, 4183. (f) Angle, S. R.; Wei, G. P.; Ko, Y. K.; Kubo, K. J. Am. Chem. Soc. 1995, 117, 8041. (g) Gurjar, M. K.; Mainkar, P. S. Heterocycles 1990, 31, 407. (h) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149. (i) Bonnaffé, D.; Simon, H. Tetrahedron 1992, 49, 9695. (j) Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1997, 53, 4339.
    • (1997) Tetrahedron , vol.53 , pp. 4339
    • Andrey, O.1    Ducry, L.2    Landais, Y.3    Planchenault, D.4    Weber, V.5
  • 33
    • 0001431501 scopus 로고
    • Alexakis, A.; Mutti, S.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 437. For the preparation of the auxiliary, see: Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 5754
    • Hanessian, S.1    Delorme, D.2    Beaudoin, S.3    Leblanc, Y.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.