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Volumn 38, Issue 16, 1997, Pages 2895-2898

Efficient methodology for the construction of substituted spiroketals. Model studies towards the synthesis of the eastern spiroketal subunit of okadaic acid.

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; OKADAIC ACID; SPIRO COMPOUND;

EID: 0030914060     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00470-X     Document Type: Article
Times cited : (40)

References (25)
  • 4
    • 85008014440 scopus 로고
    • Although okadaic acid was isolated from marine sponges, contaminating dinoflagellates are responsible for the production of this toxin. Murakami, Y.; Oshima, Y.; Yasumoto, T. Bull. Japan Soc. Sci. Fish., 1982, 48, 69. For an excellent review on Ciguatera and its off-shoots, see. Scheuer, P.J. Tetrahedron, 1994, 50, 3.
    • (1982) Bull. Japan Soc. Sci. Fish. , vol.48 , pp. 69
    • Murakami, Y.1    Oshima, Y.2    Yasumoto, T.3
  • 5
    • 0028008326 scopus 로고
    • Although okadaic acid was isolated from marine sponges, contaminating dinoflagellates are responsible for the production of this toxin. Murakami, Y.; Oshima, Y.; Yasumoto, T. Bull. Japan Soc. Sci. Fish., 1982, 48, 69. For an excellent review on Ciguatera and its off-shoots, see. Scheuer, P.J. Tetrahedron, 1994, 50, 3.
    • (1994) Tetrahedron , vol.50 , pp. 3
    • Scheuer, P.J.1
  • 9
    • 0025181418 scopus 로고
    • introductory issue
    • Cohen, P.; Holmes, C.F.B.; Tsukitani, Y. Trends Biochem. Sci., 1990, 15, 98. See also: Brugge, J.S. Chem. Biol., 1994, introductory issue.
    • (1994) Chem. Biol.
    • Brugge, J.S.1
  • 15
    • 0343298513 scopus 로고    scopus 로고
    • note
    • 4, followed by opening of the heterocycle generates the oxonium ion 21 which is then intercepted by the incipient allylic residue. (Formula Represented)
  • 16
    • 0343734174 scopus 로고    scopus 로고
    • note
    • The observed stereochemistry corroborates the observations of Taddei and Ricci and is easily deduced from the analysis of the NMR spectra of compounds 12. It originates from the chair-like transition state 21.
  • 22
    • 0343298511 scopus 로고    scopus 로고
    • This failure was also noticed by Taddei and Ricci (Taddei, M., Personal communication)
    • This failure was also noticed by Taddei and Ricci (Taddei, M., Personal communication).
  • 23
    • 0343734171 scopus 로고    scopus 로고
    • note
    • 2 = 4.4 Hz) in compounds 10, thus unambiguously positioning the choride and methyl substituents in an equatorial and axial position respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.