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Volumn 47, Issue 5, 2006, Pages 747-751

Synthesis of the common FGHI-ring part of ciguatoxins

Author keywords

Ciguatoxin; Convergent synthesis; Natural product synthesis; trans Fused polycyclic ether

Indexed keywords

CIGUATOXIN; EPOXIDE;

EID: 29644445512     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.085     Document Type: Article
Times cited : (11)

References (69)
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    • For reviews of ciguatoxins and related marine toxins, see: Y. Shimizu Chem. Rev. 93 1993 1685
    • (1993) Chem. Rev. , vol.93 , pp. 1685
    • Shimizu, Y.1
  • 47
    • 0037453554 scopus 로고    scopus 로고
    • A similar ring closure of the G-ring part by reductive etherification was reported by the Isobe group, where the cyclization of a tricyclic compound corresponding to the EF-H-ring part having 26-keto and 31-hydroxy groups was successfully performed: S. Takai, N. Sawada, and M. Isobe J. Org. Chem. 68 2003 3225
    • (2003) J. Org. Chem. , vol.68 , pp. 3225
    • Takai, S.1    Sawada, N.2    Isobe, M.3
  • 48
    • 0034644383 scopus 로고    scopus 로고
    • Although the use of the cis-epoxide (C29-epi-4 ) corresponding to 4 might be straightforward and exclude the C29-inversion step, the cis-epoxide could not be prepared so far because of the difficulty in the synthesis of the Z-iodoalkene corresponding to 6. For successful synthesis of a Z-iodoalkene, see: A.B. Smith III, T.J. Beauchamp, M.J. LaMarche, M.D. Kaufman, Y. Qiu, H. Arimoto, D.R. Jones, and K. Kobayashi J. Am. Chem. Soc. 122 2000 8654
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8654
    • Smith III, A.B.1    Beauchamp, T.J.2    Lamarche, M.J.3    Kaufman, M.D.4    Qiu, Y.5    Arimoto, H.6    Jones, D.R.7    Kobayashi, K.8
  • 61
    • 2142858450 scopus 로고
    • Since the R-configuration at C31 of 25 was proved by modified Mosher's method, the C31-configuration of the other diastereomer 24 was determined as S. For modified Mosher's method, see: I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakisawa J. Am. Chem. Soc. 113 1991 4092
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4092
    • Ohtani, I.1    Kusumi, T.2    Kashman, Y.3    Kakisawa, H.4
  • 62
    • 29644442511 scopus 로고    scopus 로고
    • note
    • The reduction of the ketone prepared from 25 was examined with several reductants, where L-Selectride® gave the best yield and selectivity of 24. The results also suggested that the selectivity of 24 increased with increasing bulkiness of the reductant. However, the reasons for the high stereoselectivity and the stereochemical preference in the reduction with bulky reductants were unclear.
  • 65
    • 29644442250 scopus 로고    scopus 로고
    • note
    • The net product ratio of 32 to 31 from 30 was determined as 2:1 by the reduction of pure 30, prepared alternatively, under the same conditions.
  • 69
    • 29644448309 scopus 로고    scopus 로고
    • note
    • +]: 1078.3230, found: 1078.3217.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.