메뉴 건너뛰기




Volumn 38, Issue 10, 1997, Pages 1693-1696

An efficient formal synthesis of balanol via the asymmetric epoxide ring opening reaction

Author keywords

[No Author keywords available]

Indexed keywords

BALANOL;

EID: 0031562447     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00192-5     Document Type: Article
Times cited : (86)

References (27)
  • 1
    • 0011432222 scopus 로고    scopus 로고
    • Dedicated to the memory of Prof. Henry C. Wu
    • (1) Dedicated to the memory of Prof. Henry C. Wu
  • 2
  • 7
    • 0345664754 scopus 로고
    • (5) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. For recent synthetic applications, see Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389; Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937; and Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5897
    • Martínez, L.E.1    Leighton, J.L.2    Carsten, D.H.3    Jacobsen, E.N.4
  • 8
    • 0030070775 scopus 로고    scopus 로고
    • (5) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. For recent synthetic applications, see Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389; Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937; and Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963.
    • (1996) J. Org. Chem. , vol.61 , pp. 389
    • Leighton, J.L.1    Jacobsen, E.N.2
  • 9
    • 0030605102 scopus 로고    scopus 로고
    • (5) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. For recent synthetic applications, see Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389; Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937; and Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7937
    • Schaus, S.E.1    Jacobsen, E.N.2
  • 10
    • 0039094109 scopus 로고    scopus 로고
    • (5) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. For recent synthetic applications, see Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389; Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937; and Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963.
    • (1996) J. Org. Chem. , vol.61 , pp. 7963
    • Martínez, L.E.1    Nugent, W.A.2    Jacobsen, E.N.3
  • 13
    • 37049080108 scopus 로고
    • (c) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc. Perkin Trans I 1995, 2355. For syntheses of the hexahydroazepine core, see: Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061.; Hong, H.; Jagdmann, G. E.; Hughes, P. F.; Nichols, J. B. Tetrahedron Lett. 1995, 36, 3659; Tuch, A.; Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29; and Sanière, M.; Le Merrer, Y.; Depezay, J. Tetrahedron Asymm. 1996, 7, 2901.
    • (1995) J. Chem. Soc. Perkin Trans I , pp. 2355
    • Adams, C.P.1    Fairway, S.M.2    Hardy, C.J.3    Hibbs, D.E.4    Hursthouse, M.B.5    Morley, A.D.6    Sharp, B.W.7    Vicker, N.8    Warner, I.9
  • 14
    • 0029018955 scopus 로고
    • (c) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc. Perkin Trans I 1995, 2355. For syntheses of the hexahydroazepine core, see: Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061.; Hong, H.; Jagdmann, G. E.; Hughes, P. F.; Nichols, J. B. Tetrahedron Lett. 1995, 36, 3659; Tuch, A.; Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29; and Sanière, M.; Le Merrer, Y.; Depezay, J. Tetrahedron Asymm. 1996, 7, 2901.
    • (1995) Tetrahedron , vol.51 , pp. 6061
    • Tanner, D.1    Almario, A.2    Högberg, T.3
  • 15
    • 0029018846 scopus 로고
    • (c) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc. Perkin Trans I 1995, 2355. For syntheses of the hexahydroazepine core, see: Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061.; Hong, H.; Jagdmann, G. E.; Hughes, P. F.; Nichols, J. B. Tetrahedron Lett. 1995, 36, 3659; Tuch, A.; Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29; and Sanière, M.; Le Merrer, Y.; Depezay, J. Tetrahedron Asymm. 1996, 7, 2901.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3659
    • Hong, H.1    Jagdmann, G.E.2    Hughes, P.F.3    Nichols, J.B.4
  • 16
    • 0011387836 scopus 로고    scopus 로고
    • (c) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc. Perkin Trans I 1995, 2355. For syntheses of the hexahydroazepine core, see: Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061.; Hong, H.; Jagdmann, G. E.; Hughes, P. F.; Nichols, J. B. Tetrahedron Lett. 1995, 36, 3659; Tuch, A.; Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29; and Sanière, M.; Le Merrer, Y.; Depezay, J. Tetrahedron Asymm. 1996, 7, 2901.
    • (1996) Synlett , pp. 29
    • Tuch, A.1    Albertini, E.2    Barco, A.3    Benetti, S.4    De Risi, C.5    Pollini, G.P.6    Zanirato, V.7
  • 17
    • 0030272833 scopus 로고    scopus 로고
    • (c) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc. Perkin Trans I 1995, 2355. For syntheses of the hexahydroazepine core, see: Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061.; Hong, H.; Jagdmann, G. E.; Hughes, P. F.; Nichols, J. B. Tetrahedron Lett. 1995, 36, 3659; Tuch, A.; Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29; and Sanière, M.; Le Merrer, Y.; Depezay, J. Tetrahedron Asymm. 1996, 7, 2901.
    • (1996) Tetrahedron Asymm. , vol.7 , pp. 2901
    • Sanière, M.1    Le Merrer, Y.2    Depezay, J.3
  • 20
    • 0000269981 scopus 로고
    • (9) The high regioselectivity of the nucleophilic attack is attributed to the preferred diaxial opening of conformationally constrained cyclohexene oxides. See Fürst, A.; Plattner, P. A. Helv. Chim. Acta 1949, 32, 275.
    • (1949) Helv. Chim. Acta , vol.32 , pp. 275
    • Fürst, A.1    Plattner, P.A.2
  • 22
    • 0011477353 scopus 로고    scopus 로고
    • The structure of 8 was confirmed by homonuclear decoupling experiments on the acetate ester
    • (11) The structure of 8 was confirmed by homonuclear decoupling experiments on the acetate ester.
  • 23
    • 84910971057 scopus 로고
    • (12) Although no definitive stereochemical assignment was made, the major oxime is presumed to bear the sulfonate ester anti to the olefinic carbon; the observed isomeric product ratio is in line with results of previous studies on cyclohexenone oximes by Shoppee, C. W.; Akhtar, M. I.; Lack, R. E. J. Chem. Soc. 1964, 3392.
    • (1964) J. Chem. Soc. , pp. 3392
    • Shoppee, C.W.1    Akhtar, M.I.2    Lack, R.E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.