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Volumn 43, Issue 36, 2004, Pages 4782-4785

An efficient total synthesis of optically active tetrodotoxin

Author keywords

Guanidine; Ion channels; Natural products; Tetrodotoxin; Total synthesis

Indexed keywords

MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL);

EID: 4644371696     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460293     Document Type: Article
Times cited : (99)

References (45)
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    • (1986) Ann. Ni Y. Acad. Sci. , vol.479
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    • (1994) Angew. Chem. , vol.106 , pp. 23
    • Hucho, F.1
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    • b) F. Hucho, Angew. Chem. 1994, 106, 23; Angew. Chem. Int. Ed. Engl. 1995, 34, 39-50.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 39-50
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    • K. Matsumura, Nature 1995, 378, 563-564.
    • (1995) Nature , vol.378 , pp. 563-564
    • Matsumura, K.1
  • 29
    • 0033581622 scopus 로고    scopus 로고
    • a) T. Nishikawa, M. Asai, N. Ohyabu, N. Yamamoto, M. Isobe, Angew. Chem. 1999, 111, 3268-3271; Angew. Chem. Int. Ed. 1999, 38, 3081-3084;
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3081-3084
  • 36
    • 4644351085 scopus 로고    scopus 로고
    • note
    • The configuration of the major product could not be determined at this stage.
  • 37
    • 4644332240 scopus 로고    scopus 로고
    • note
    • The structure was confirmed by the methylation of 15 with TMS-CHN2.
  • 39
    • 4644296172 scopus 로고    scopus 로고
    • note
    • The configuration at C9 was established based on the long-range coupling (J = 1 Hz) between 9-H and 4a-H.
  • 40
    • 4644245963 scopus 로고    scopus 로고
    • note
    • 13C NMR spectroscopy; δ = 108.2 ppm for compound 20, δ = 108.5 ppm for compound 23.
  • 42
    • 4644288409 scopus 로고    scopus 로고
    • note
    • The configuration of the acetal was determined as shown in Scheme 3 based on the coupling constant for 4-H and 4a-H; see reference [13].
  • 43
    • 4644275774 scopus 로고    scopus 로고
    • note
    • The temperature was important for obtaining the amine in good yield. At an elevated temperature (around O°C) the product was obtained in very low yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.