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Volumn 5, Issue 10, 2003, Pages 1697-1700

Common-intermediate strategy for synthesis of conduritols and inositols via β-hydroxy cyclohexenylsilanes

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; CONDURITOL A; CONDURITOL B; CONDURITOL C; CONDURITOL D; CONDURITOL E; CONDURITOL F; GLYCOSIDASE INHIBITOR; INOSITOL DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG; CYCLOHEXANOL DERIVATIVE; CYCLOHEXENE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; INOSITOL;

EID: 0042519554     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034349d     Document Type: Article
Times cited : (39)

References (57)
  • 1
    • 0001836318 scopus 로고    scopus 로고
    • and references therein
    • (a) Balci, M. Pure Appl. Chem. 1997, 69, 97 and references therein.
    • (1997) Pure Appl. Chem. , vol.69 , pp. 97
    • Balci, M.1
  • 16
    • 0037013888 scopus 로고    scopus 로고
    • For recent examples, see: (a) de Sousa, S. E.; O'Brien, P.; Pilgram, C. D. Tetrahedron 2002, 58, 4643. (b) Kadota, K.; Takeuchi, M.; Taniguchi, T.; Ogawawara, K. Org. Lett. 2001, 3, 1769. (c) Ceré, V.; Mantovani, G.; Peri, F.; Pollicino, S.; Ricci, A. Tetrahedron 2000, 56, 1225. (d) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995.
    • (2002) Tetrahedron , vol.58 , pp. 4643
    • De Sousa, S.E.1    O'Brien, P.2    Pilgram, C.D.3
  • 17
    • 0000102073 scopus 로고    scopus 로고
    • For recent examples, see: (a) de Sousa, S. E.; O'Brien, P.; Pilgram, C. D. Tetrahedron 2002, 58, 4643. (b) Kadota, K.; Takeuchi, M.; Taniguchi, T.; Ogawawara, K. Org. Lett. 2001, 3, 1769. (c) Ceré, V.; Mantovani, G.; Peri, F.; Pollicino, S.; Ricci, A. Tetrahedron 2000, 56, 1225. (d) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995.
    • (2001) Org. Lett. , vol.3 , pp. 1769
    • Kadota, K.1    Takeuchi, M.2    Taniguchi, T.3    Ogawawara, K.4
  • 18
    • 0034712221 scopus 로고    scopus 로고
    • For recent examples, see: (a) de Sousa, S. E.; O'Brien, P.; Pilgram, C. D. Tetrahedron 2002, 58, 4643. (b) Kadota, K.; Takeuchi, M.; Taniguchi, T.; Ogawawara, K. Org. Lett. 2001, 3, 1769. (c) Ceré, V.; Mantovani, G.; Peri, F.; Pollicino, S.; Ricci, A. Tetrahedron 2000, 56, 1225. (d) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995.
    • (2000) Tetrahedron , vol.56 , pp. 1225
    • Ceré, V.1    Mantovani, G.2    Peri, F.3    Pollicino, S.4    Ricci, A.5
  • 19
    • 0025002572 scopus 로고
    • For recent examples, see: (a) de Sousa, S. E.; O'Brien, P.; Pilgram, C. D. Tetrahedron 2002, 58, 4643. (b) Kadota, K.; Takeuchi, M.; Taniguchi, T.; Ogawawara, K. Org. Lett. 2001, 3, 1769. (c) Ceré, V.; Mantovani, G.; Peri, F.; Pollicino, S.; Ricci, A. Tetrahedron 2000, 56, 1225. (d) Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F. Tetrahedron 1990, 46, 4995.
    • (1990) Tetrahedron , vol.46 , pp. 4995
    • Ley, S.V.1    Parra, M.2    Redgrave, A.J.3    Sternfeld, F.4
  • 32
    • 0035917329 scopus 로고    scopus 로고
    • For recent examples, see: (a) Takahashi, H.; Kittaka, H.; Ikegami, S. J. Org. Chem. 2001, 66, 2705. (b) Angleaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (c) Riley, A. M.; Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1998, 314, 277. (d) Husson, C.; Odier, L.; Vottéro, P. J. A. Carbohydr. Res. 1998, 307, 163. (e) Gigg, J.; Gigg, R. Carbohydr. Res. 1997, 299, 77. (f) Desjardins, M.; Brammer, L. E., Jr.; Hudlicky, T. Carbohydr. Res. 1997, 304, 39. (g) Angyal, S. J.; Odier, L.; Tate, M. E. Carbohydr. Res. 1995, 266, 143. (h) Bruzik, K. S.; Tsai, M.-D. J. Am. Chem. Soc. 1992, 114, 6361.
    • (2001) J. Org. Chem. , vol.66 , pp. 2705
    • Takahashi, H.1    Kittaka, H.2    Ikegami, S.3
  • 33
    • 0033601314 scopus 로고    scopus 로고
    • For recent examples, see: (a) Takahashi, H.; Kittaka, H.; Ikegami, S. J. Org. Chem. 2001, 66, 2705. (b) Angleaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (c) Riley, A. M.; Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1998, 314, 277. (d) Husson, C.; Odier, L.; Vottéro, P. J. A. Carbohydr. Res. 1998, 307, 163. (e) Gigg, J.; Gigg, R. Carbohydr. Res. 1997, 299, 77. (f) Desjardins, M.; Brammer, L. E., Jr.; Hudlicky, T. Carbohydr. Res. 1997, 304, 39. (g) Angyal, S. J.; Odier, L.; Tate, M. E. Carbohydr. Res. 1995, 266, 143. (h) Bruzik, K. S.; Tsai, M.-D. J. Am. Chem. Soc. 1992, 114, 6361.
    • (1999) J. Org. Chem. , vol.64 , pp. 9613
    • Angleaud, R.1    Babot, O.2    Charvat, T.3    Landais, Y.4
  • 34
    • 0032440268 scopus 로고    scopus 로고
    • For recent examples, see: (a) Takahashi, H.; Kittaka, H.; Ikegami, S. J. Org. Chem. 2001, 66, 2705. (b) Angleaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (c) Riley, A. M.; Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1998, 314, 277. (d) Husson, C.; Odier, L.; Vottéro, P. J. A. Carbohydr. Res. 1998, 307, 163. (e) Gigg, J.; Gigg, R. Carbohydr. Res. 1997, 299, 77. (f) Desjardins, M.; Brammer, L. E., Jr.; Hudlicky, T. Carbohydr. Res. 1997, 304, 39. (g) Angyal, S. J.; Odier, L.; Tate, M. E. Carbohydr. Res. 1995, 266, 143. (h) Bruzik, K. S.; Tsai, M.-D. J. Am. Chem. Soc. 1992, 114, 6361.
    • (1998) Carbohydr. Res. , vol.314 , pp. 277
    • Riley, A.M.1    Jenkins, D.J.2    Potter, B.V.L.3
  • 35
    • 0032004199 scopus 로고    scopus 로고
    • For recent examples, see: (a) Takahashi, H.; Kittaka, H.; Ikegami, S. J. Org. Chem. 2001, 66, 2705. (b) Angleaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (c) Riley, A. M.; Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1998, 314, 277. (d) Husson, C.; Odier, L.; Vottéro, P. J. A. Carbohydr. Res. 1998, 307, 163. (e) Gigg, J.; Gigg, R. Carbohydr. Res. 1997, 299, 77. (f) Desjardins, M.; Brammer, L. E., Jr.; Hudlicky, T. Carbohydr. Res. 1997, 304, 39. (g) Angyal, S. J.; Odier, L.; Tate, M. E. Carbohydr. Res. 1995, 266, 143. (h) Bruzik, K. S.; Tsai, M.-D. J. Am. Chem. Soc. 1992, 114, 6361.
    • (1998) Carbohydr. Res. , vol.307 , pp. 163
    • Husson, C.1    Odier, L.2    Vottéro, P.J.A.3
  • 36
    • 0030890593 scopus 로고    scopus 로고
    • For recent examples, see: (a) Takahashi, H.; Kittaka, H.; Ikegami, S. J. Org. Chem. 2001, 66, 2705. (b) Angleaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (c) Riley, A. M.; Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1998, 314, 277. (d) Husson, C.; Odier, L.; Vottéro, P. J. A. Carbohydr. Res. 1998, 307, 163. (e) Gigg, J.; Gigg, R. Carbohydr. Res. 1997, 299, 77. (f) Desjardins, M.; Brammer, L. E., Jr.; Hudlicky, T. Carbohydr. Res. 1997, 304, 39. (g) Angyal, S. J.; Odier, L.; Tate, M. E. Carbohydr. Res. 1995, 266, 143. (h) Bruzik, K. S.; Tsai, M.-D. J. Am. Chem. Soc. 1992, 114, 6361.
    • (1997) Carbohydr. Res. , vol.299 , pp. 77
    • Gigg, J.1    Gigg, R.2
  • 37
    • 0030830773 scopus 로고    scopus 로고
    • For recent examples, see: (a) Takahashi, H.; Kittaka, H.; Ikegami, S. J. Org. Chem. 2001, 66, 2705. (b) Angleaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (c) Riley, A. M.; Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1998, 314, 277. (d) Husson, C.; Odier, L.; Vottéro, P. J. A. Carbohydr. Res. 1998, 307, 163. (e) Gigg, J.; Gigg, R. Carbohydr. Res. 1997, 299, 77. (f) Desjardins, M.; Brammer, L. E., Jr.; Hudlicky, T. Carbohydr. Res. 1997, 304, 39. (g) Angyal, S. J.; Odier, L.; Tate, M. E. Carbohydr. Res. 1995, 266, 143. (h) Bruzik, K. S.; Tsai, M.-D. J. Am. Chem. Soc. 1992, 114, 6361.
    • (1997) Carbohydr. Res. , vol.304 , pp. 39
    • Desjardins, M.1    Brammer L.E., Jr.2    Hudlicky, T.3
  • 38
    • 0029633809 scopus 로고
    • For recent examples, see: (a) Takahashi, H.; Kittaka, H.; Ikegami, S. J. Org. Chem. 2001, 66, 2705. (b) Angleaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (c) Riley, A. M.; Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1998, 314, 277. (d) Husson, C.; Odier, L.; Vottéro, P. J. A. Carbohydr. Res. 1998, 307, 163. (e) Gigg, J.; Gigg, R. Carbohydr. Res. 1997, 299, 77. (f) Desjardins, M.; Brammer, L. E., Jr.; Hudlicky, T. Carbohydr. Res. 1997, 304, 39. (g) Angyal, S. J.; Odier, L.; Tate, M. E. Carbohydr. Res. 1995, 266, 143. (h) Bruzik, K. S.; Tsai, M.-D. J. Am. Chem. Soc. 1992, 114, 6361.
    • (1995) Carbohydr. Res. , vol.266 , pp. 143
    • Angyal, S.J.1    Odier, L.2    Tate, M.E.3
  • 39
    • 0001347785 scopus 로고
    • For recent examples, see: (a) Takahashi, H.; Kittaka, H.; Ikegami, S. J. Org. Chem. 2001, 66, 2705. (b) Angleaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613. (c) Riley, A. M.; Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1998, 314, 277. (d) Husson, C.; Odier, L.; Vottéro, P. J. A. Carbohydr. Res. 1998, 307, 163. (e) Gigg, J.; Gigg, R. Carbohydr. Res. 1997, 299, 77. (f) Desjardins, M.; Brammer, L. E., Jr.; Hudlicky, T. Carbohydr. Res. 1997, 304, 39. (g) Angyal, S. J.; Odier, L.; Tate, M. E. Carbohydr. Res. 1995, 266, 143. (h) Bruzik, K. S.; Tsai, M.-D. J. Am. Chem. Soc. 1992, 114, 6361.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6361
    • Bruzik, K.S.1    Tsai, M.-D.2
  • 47
    • 0141773513 scopus 로고    scopus 로고
    • note
    • Compound 2 constitutes a formal synthesis of D-myo-inositol-1,4,5-triphosphate 1 (Figure 2) and was in agreement with reported spectral data; see ref 9d.
  • 49
    • 0141438680 scopus 로고    scopus 로고
    • note
    • (a) KH, THF, 0°C, 8 h; 80% (2:3 = 16:1).
  • 50
    • 0141550205 scopus 로고    scopus 로고
    • note
    • (b) KHMDS, THF, -78°C, 6 h; 50-88% (2:3 = 6-20:1).
  • 51
    • 0141773512 scopus 로고    scopus 로고
    • note
    • tBu, THF, 0°C, 2 h; 33% (2:3 = 6:1).
  • 52
    • 0141661585 scopus 로고    scopus 로고
    • note
    • tBu, 18-C-6, THF, 0°C, 1 h; 58% (2:3 = 16:1).
  • 54
    • 0141550204 scopus 로고    scopus 로고
    • note
    • 13C NMR, optical rotation, and HRMS compared to literature values.
  • 55
    • 0141773511 scopus 로고    scopus 로고
    • note
    • Diastereoselectivity of silylallylboration en route to the stereotetrad in 11 has been improved by using the acetonide-protected aldehyde 21 (cf. 8), which gave β-hydroxyallylsilane 22 with > 15:1 dr. Compound 22 readily underwent RCM to provide cyclohexene 23 in good yield. Further elaboration of 23 to cyclitol derivatives will be reported in our subsequent papers in this series.


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