메뉴 건너뛰기




Volumn 44, Issue 46, 2003, Pages 8365-8368

Highly functionalized trans-2,5-disubstituted tetrahydrofurans from ribofuranoside templates: Precursors to linked polycyclic ethers

Author keywords

Acetogenins; Iodoetherification; Polyethers; Tetrahydrofuran

Indexed keywords

ETHER DERIVATIVE; FURAN DERIVATIVE; MONENSIN DERIVATIVE; POLYCYCLIC HYDROCARBON; RIBOFURANOSIDE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0141887612     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.126     Document Type: Article
Times cited : (4)

References (44)
  • 9
    • 33845555768 scopus 로고
    • For seminal studies on the iodoetherification of 5-alkoxyalkene derivatives: Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963-3964; (b) Bartlett, P. A.; Richardson, D. P.; Myerson, J. Tetrahedron 1984, 40, 2317-2328. Reviews: (c) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711-1754; (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321-3408.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3963-3964
    • Rychnovsky, S.D.1    Bartlett, P.A.2
  • 10
    • 0001631004 scopus 로고
    • For seminal studies on the iodoetherification of 5-alkoxyalkene derivatives: Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963-3964; (b) Bartlett, P. A.; Richardson, D. P.; Myerson, J. Tetrahedron 1984, 40, 2317-2328. Reviews: (c) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711-1754; (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321-3408.
    • (1984) Tetrahedron , vol.40 , pp. 2317-2328
    • Bartlett, P.A.1    Richardson, D.P.2    Myerson, J.3
  • 11
    • 0027200955 scopus 로고
    • For seminal studies on the iodoetherification of 5-alkoxyalkene derivatives: Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963-3964; (b) Bartlett, P. A.; Richardson, D. P.; Myerson, J. Tetrahedron 1984, 40, 2317-2328. Reviews: (c) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711-1754; (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321-3408.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1711-1754
    • Harmange, J.-C.1    Figadère, B.2
  • 12
    • 0001657273 scopus 로고
    • For seminal studies on the iodoetherification of 5-alkoxyalkene derivatives: Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963-3964; (b) Bartlett, P. A.; Richardson, D. P.; Myerson, J. Tetrahedron 1984, 40, 2317-2328. Reviews: (c) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711-1754; (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321-3408.
    • (1990) Tetrahedron , vol.46 , pp. 3321-3408
    • Cardillo, G.1    Orena, M.2
  • 13
    • 0029556693 scopus 로고
    • For a related synthesis of trans-2,5-disubstituted THFs from less complex, non-carbohydrate precursors: (a) Zhang, H.; Mootoo, D. R. J. Org. Chem. 1995, 60, 8134-8135; (b) Zhang, H.; Seepersaud, M.; Seepersaud, S.; Mootoo, D. R. J. Org. Chem. 1998, 63, 2049-2052; (c) Ruan, Z.; Mootoo, D. R. Tetrahedron Lett. 1999, 40, 49-52; (d) Dabideen, D.; Ruan, Z.; Mootoo, D. R. Tetrahedron 2002, 58, 2077-2084.
    • (1995) J. Org. Chem. , vol.60 , pp. 8134-8135
    • Zhang, H.1    Mootoo, D.R.2
  • 14
    • 0032549530 scopus 로고    scopus 로고
    • For a related synthesis of trans-2,5-disubstituted THFs from less complex, non-carbohydrate precursors: (a) Zhang, H.; Mootoo, D. R. J. Org. Chem. 1995, 60, 8134-8135; (b) Zhang, H.; Seepersaud, M.; Seepersaud, S.; Mootoo, D. R. J. Org. Chem. 1998, 63, 2049-2052; (c) Ruan, Z.; Mootoo, D. R. Tetrahedron Lett. 1999, 40, 49-52; (d) Dabideen, D.; Ruan, Z.; Mootoo, D. R. Tetrahedron 2002, 58, 2077-2084.
    • (1998) J. Org. Chem. , vol.63 , pp. 2049-2052
    • Zhang, H.1    Seepersaud, M.2    Seepersaud, S.3    Mootoo, D.R.4
  • 15
    • 0032890472 scopus 로고    scopus 로고
    • For a related synthesis of trans-2,5-disubstituted THFs from less complex, non-carbohydrate precursors: (a) Zhang, H.; Mootoo, D. R. J. Org. Chem. 1995, 60, 8134-8135; (b) Zhang, H.; Seepersaud, M.; Seepersaud, S.; Mootoo, D. R. J. Org. Chem. 1998, 63, 2049-2052; (c) Ruan, Z.; Mootoo, D. R. Tetrahedron Lett. 1999, 40, 49-52; (d) Dabideen, D.; Ruan, Z.; Mootoo, D. R. Tetrahedron 2002, 58, 2077-2084.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 49-52
    • Ruan, Z.1    Mootoo, D.R.2
  • 16
    • 0037060928 scopus 로고    scopus 로고
    • For a related synthesis of trans-2,5-disubstituted THFs from less complex, non-carbohydrate precursors: (a) Zhang, H.; Mootoo, D. R. J. Org. Chem. 1995, 60, 8134-8135; (b) Zhang, H.; Seepersaud, M.; Seepersaud, S.; Mootoo, D. R. J. Org. Chem. 1998, 63, 2049-2052; (c) Ruan, Z.; Mootoo, D. R. Tetrahedron Lett. 1999, 40, 49-52; (d) Dabideen, D.; Ruan, Z.; Mootoo, D. R. Tetrahedron 2002, 58, 2077-2084.
    • (2002) Tetrahedron , vol.58 , pp. 2077-2084
    • Dabideen, D.1    Ruan, Z.2    Mootoo, D.R.3
  • 18
    • 0018427662 scopus 로고
    • Total syntheses of monensin A: (a) Fukayama, T.; Akasaka, K.; Karanewsky, D. S.; Wang, C. L. J.; Schmid, G.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 262-263; (b) Collum, D. B.; McDonald, J. H.; Still, W. C. J. Am. Chem. Soc. 1980, 102, 2120-2121; (c) Ireland, R. E.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 113, 7166-7172.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 262-263
    • Fukayama, T.1    Akasaka, K.2    Karanewsky, D.S.3    Wang, C.L.J.4    Schmid, G.5    Kishi, Y.6
  • 19
    • 0000044829 scopus 로고
    • Total syntheses of monensin A: (a) Fukayama, T.; Akasaka, K.; Karanewsky, D. S.; Wang, C. L. J.; Schmid, G.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 262-263; (b) Collum, D. B.; McDonald, J. H.; Still, W. C. J. Am. Chem. Soc. 1980, 102, 2120-2121; (c) Ireland, R. E.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 113, 7166-7172.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 2120-2121
    • Collum, D.B.1    McDonald, J.H.2    Still, W.C.3
  • 20
    • 0027255156 scopus 로고
    • Total syntheses of monensin A: (a) Fukayama, T.; Akasaka, K.; Karanewsky, D. S.; Wang, C. L. J.; Schmid, G.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 262-263; (b) Collum, D. B.; McDonald, J. H.; Still, W. C. J. Am. Chem. Soc. 1980, 102, 2120-2121; (c) Ireland, R. E.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 113, 7166-7172.
    • (1993) J. Am. Chem. Soc. , vol.113 , pp. 7166-7172
    • Ireland, R.E.1    Meissner, R.S.2    Rizzacasa, M.A.3
  • 25
    • 85009054681 scopus 로고    scopus 로고
    • note
    • 3) δ 21.2, 23.5, 24.3, 25.3, 26.8, 27.5, 32.8, 35.5, 36.9, 68.7, 84.6, 86.3, 86.8, 106.0, 112.3, 114.9, 128.2, 128.9, 130.2, 131.1, 137.4.
  • 29
    • 85009047556 scopus 로고    scopus 로고
    • note
    • + 435.1032, found 435.1032.
  • 30
    • 0028263686 scopus 로고
    • The iodocyclization of furanoside diene 22 led to a mixture 23 c/t (cis/trans, ca. 20/1). The stereochemistry of the products was assigned by conversion to aldehydes 24 c/t, and comparison of the NMR data for these derivatives with the known compounds 25 c/t (Fujimoto, Y.; Murasaki, C.; Shimada, H.; Nishioka, S.; Kakinuma, K.; Singh, S.; Singh, M.; Gupta, Y. K.; Sahai, M. Chem. Pharm. Bull. 1994, 42, 1175-1184).
    • (1994) Chem. Pharm. Bull. , vol.42 , pp. 1175-1184
    • Fujimoto, Y.1    Murasaki, C.2    Shimada, H.3    Nishioka, S.4    Kakinuma, K.5    Singh, S.6    Singh, M.7    Gupta, Y.K.8    Sahai, M.9
  • 35
    • 85009047214 scopus 로고    scopus 로고
    • note
    • + 311.1858, found 311.1857.
  • 39
    • 85009051140 scopus 로고    scopus 로고
    • note
    • + 377.1940, found 377.1939.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.