메뉴 건너뛰기




Volumn 57, Issue 21, 2001, Pages 4543-4558

Stereocontrolled synthesis of (-)-5,11-dideoxytetrodotoxin

Author keywords

Asymmetric synthesis; Guanidine; Marine metabolites; Tetrodotoxin

Indexed keywords

5,11 DIDEOXYTETRODOTOXIN; ACETAMIDE DERIVATIVE; ACETIC ACID DERIVATIVE; CARBOXYLIC ACID; FISH VENOM; GUANIDINE; TETRODOTOXIN; UNCLASSIFIED DRUG;

EID: 0035927211     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)00382-9     Document Type: Article
Times cited : (48)

References (60)
  • 1
    • 0023032629 scopus 로고
    • Tetrodotoxin, Saxitoxin, and the Molecular Biology of the Sodium Channel
    • Review: (a) Eds
    • Review: (a) Tetrodotoxin, Saxitoxin, and the Molecular Biology of the Sodium Channel. Kao, C. Y., Lovinson, S., Eds. Ann. N.Y., Acad. Sci. New York, 1986, 479, 1-355.
    • (1986) Ann. N.Y., Acad. Sci. New York , vol.479 , pp. 1-355
    • Kao, C.Y.1    Lovinson, S.2
  • 9
    • 0023032629 scopus 로고
    • Tetrodotoxin, Saxitoxin, and the Molecular Biology of the Sodium Channel
    • Kao, C. Y., Lovinson, S., Eds
    • Fuhrman, F. A. Tetrodotoxin, Saxitoxin, and the Molecular Biology of the Sodium Channel. Kao, C. Y., Lovinson, S., Eds. Ann. N.Y. Acad. Sci. New York 1986, 479, 1-14.
    • (1986) Ann. N.Y. Acad. Sci. New York , vol.479 , pp. 1-14
    • Fuhrman, F.A.1
  • 11
    • 0343905314 scopus 로고
    • (b) 1-Hydroxy-5,11-dideoxytetrodotoxin (5)
    • (b) 1-Hydroxy-5,11-dideoxytetrodotoxin (5): Kotaki Y., Shimizu Y. J. Am. Chem. Soc. 115:1993;827-830.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 827-830
    • Kotaki, Y.1    Shimizu, Y.2
  • 12
    • 33845280591 scopus 로고
    • (c) 11-Deoxytetrodotoxin (3) and 6-epi-17-tetrodotoxin
    • (c) 11-Deoxytetrodotoxin (3) and 6-epi-17-tetrodotoxin: Yasumoto T., Yotsu M., Murata M., Naoki M. J. Am. Chem. Soc. 110:1988;2344-2345.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 2344-2345
    • Yasumoto, T.1    Yotsu, M.2    Murata, M.3    Naoki, M.4
  • 19
  • 23
    • 0034703414 scopus 로고    scopus 로고
    • For leading references from other laboratories, see: (a)
    • For leading references from other laboratories, see: (a) Noya B., Paredes M.D., Ozores L., Alonso R. J. Org. Chem. 65:2000;5960-5968.
    • (2000) J. Org. Chem. , vol.65 , pp. 5960-5968
    • Noya, B.1    Paredes, M.D.2    Ozores, L.3    Alonso, R.4
  • 28
    • 84991416324 scopus 로고
    • Ph.D. Thesis, Harvard University
    • Upreslacis, J., Ph.D. Thesis, Harvard University, 1975.
    • (1975)
    • Upreslacis, J.1
  • 39
  • 40
    • 0343490662 scopus 로고    scopus 로고
    • G. Helmchen, R.W. Hoffmann, J. Mulzer, Schaumann E. Stuttgart: Thieme
    • Woggon W.-D. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E. Stereoselective Synthesis E 21 (Houben-Weyl.). Vol. 8:1996;4947-4956 Thieme, Stuttgart.
    • (1996) Stereoselective Synthesis e 21 (Houben-Weyl.) , vol.8 , pp. 4947-4956
    • Woggon, W.-D.1
  • 41
    • 49149145492 scopus 로고
    • N2′ reactions, see
    • N2′ reactions, see: Magid R.M. Tetrahedron. 36:1980;1901-1930.
    • (1980) Tetrahedron , vol.36 , pp. 1901-1930
    • Magid, R.M.1
  • 42
    • 84991427082 scopus 로고    scopus 로고
    • eq. The diaxial orientation of these two bromides seems to be compensated due to their dipole-dipole interaction
    • eq. The diaxial orientation of these two bromides seems to be compensated due to their dipole-dipole interaction.
  • 57
    • 0343926363 scopus 로고
    • The lability of the acetoxy group at the C-9 position was reported in Kishi's total synthesis of tetrodotoxin. See: (a) Ref. 13(b). (b)
    • The lability of the acetoxy group at the C-9 position was reported in Kishi's total synthesis of tetrodotoxin. See: (a) Ref. 13(b). (b) Tanino H., Inoue S., Aratani M., Kishi Y. Tetrahedron Lett. 15:1974;335-338.
    • (1974) Tetrahedron Lett. , vol.15 , pp. 335-338
    • Tanino, H.1    Inoue, S.2    Aratani, M.3    Kishi, Y.4
  • 60
    • 84991415699 scopus 로고    scopus 로고
    • 3N used in the model experiments gave unreproducible results
    • 3N used in the model experiments gave unreproducible results.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.