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Volumn , Issue 6, 2000, Pages 610-611

Asymmetric synthesis of the A-ring part of ciguatoxin by the strategy based on diastereoselective hydroboration and ring closing metathesis

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EID: 0034335709     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.610     Document Type: Article
Times cited : (35)

References (71)
  • 1
    • 1542502091 scopus 로고
    • For reviews on ciguatoxins and related compounds, see: a) T. Yasumoto and M. Murata, Chem. Rev., 93, 1897 (1993).
    • (1993) Chem. Rev. , vol.93 , pp. 1897
    • Yasumoto, T.1    Murata, M.2
  • 4
    • 0001863039 scopus 로고    scopus 로고
    • For our synthetic studies on 1, see: a) T. Oka and A. Murai, Chem. Lett., 1994, 1611.
    • Chem. Lett. , vol.1994 , pp. 1611
    • Oka, T.1    Murai, A.2
  • 20
    • 0033525470 scopus 로고    scopus 로고
    • See also Ref. 2d, 2f, and 5
    • k) R. Saeeng and M. Isobe, Tetrahedron Lett., 40, 1911 (1999). See also Ref. 2d, 2f, and 5.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 1911
    • Saeeng, R.1    Isobe, M.2
  • 42
    • 0032580376 scopus 로고    scopus 로고
    • For reviews on ring-closing metathesis, see: a) R. H. Grubbs and S. Chang, Tetrahedron, 54, 4413 (1998).
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 57
    • 0001943172 scopus 로고    scopus 로고
    • note
    • Position numberings in this letter are according to those of CTX1 B.
  • 62
    • 0032806956 scopus 로고    scopus 로고
    • 4; BnBr, t-BuOK, TBAI; 6M HCl-THF (1:1); 83% total yield] from (2S, 3R)-2-(2-propenyl)-3-hydroxyoxane (98%ee) which was synthesized according to the following paper: K. Fujiwara, K. Saka, D. Takaoka, and A. Murai, Synlett, 1999, 1037.
    • Synlett , vol.1999 , pp. 1037
    • Fujiwara, K.1    Saka, K.2    Takaoka, D.3    Murai, A.4
  • 69
    • 0001791203 scopus 로고    scopus 로고
    • note
    • Treatment of 8a or 8b with thexylborane followed by oxidation could not improve the ratio of 9 to 10. In each case, the production of 5, which would resulted from 1,2-elimination in the corresponding hydroboration product having a 2-alkoxyalkylborane system, was mainly observed.
  • 71
    • 84985702456 scopus 로고    scopus 로고
    • was applied to diol 20b, the reaction could not finish and gave a mixture of the corresponding iodide and 21b. Further treatment of the mixture with Zn was required for the complete conversion to 21b
    • When Samuelsson's method (P. J. Garegg and B. Samuelsson, Synthesis, 1979, 469) was applied to diol 20b, the reaction could not finish and gave a mixture of the corresponding iodide and 21b. Further treatment of the mixture with Zn was required for the complete conversion to 21b.
    • Synthesis , vol.1979 , pp. 469
    • Garegg, P.J.1    Samuelsson, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.