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Volumn 73, Issue 4, 2008, Pages 1234-1242

Stereoselective and efficient total synthesis of optically active tetrodotoxin from D-glucose

Author keywords

[No Author keywords available]

Indexed keywords

REACTION KINETICS; STEREOSELECTIVITY;

EID: 39349084860     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701655v     Document Type: Article
Times cited : (75)

References (78)
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    • For examples of TTX analogues, 5,6,11-trideoxyTTX: (a) Yotsu-Yamashita, M.; Yamagishi, Y.; Yasumoto, T. Tetrahedron Lett. 1995, 36, 9329-9332.
  • 18
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    • 1-Hydroxy-5,11-dideoxyTTX: (d) Kotaki, Y.; Shimizu, Y. J. Am. Chem. Soc. 1993, 115, 827-830.
    • 1-Hydroxy-5,11-dideoxyTTX: (d) Kotaki, Y.; Shimizu, Y. J. Am. Chem. Soc. 1993, 115, 827-830.
  • 19
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    • 4-epiTTX: (e) Yasumoto, T.; Michishita, T. Agric. Biol. Chem. 1985, 49, 3077-3088.
  • 20
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    • 6-epiTTX, 11-deoxyTTX: (f) Yasumoto, T.; Yotsu, M.; Murata, M.; Naoki, H. J. Am. Chem. Soc. 1988, 110, 2344-2345.
    • 6-epiTTX, 11-deoxyTTX: (f) Yasumoto, T.; Yotsu, M.; Murata, M.; Naoki, H. J. Am. Chem. Soc. 1988, 110, 2344-2345.
  • 21
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    • 8,11-dideoxyTTX: (g) Nishikawa, T.; Urabe, D.; Yoshida, K.; Iwabuchi, T.; Asai, M.; Isobe, M. Chem. Eur. J. 2004, 10, 452-462.
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    • 11-oxoTTX: (i) Khora, S. S.; Yasumoto, T. Tetrahedron Lett. 1989, 30, 4393-4394. 11-norTTX-6(R)-ol:
  • 25
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    • 11-norTTX-6(S)-ol: (k) Yotsu, M.; Hayashi, Y.; Khora, S. S.; Sato, S.; Yasumoto, T. Biosci. Biotechnol. Biochem. 1992, 56, 370-371.
    • 11-norTTX-6(S)-ol: (k) Yotsu, M.; Hayashi, Y.; Khora, S. S.; Sato, S.; Yasumoto, T. Biosci. Biotechnol. Biochem. 1992, 56, 370-371.
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    • Several TTX analogues
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    • For review of the Henry reaction see
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    • Luzzio, F.A.1
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    • The IUPAC name of compound 11 is 1-L-(1,2,3′,4,5/3, 6)-3-hydroxymethyl-3,3′-di-O-benzyl-6-nitro-2,3,4, 5-tetrahydroxycyclohexane-carbaldehyde diphenyldithioacetal.
    • The IUPAC name of compound 11 is 1-L-(1,2,3′,4,5/3, 6)-3-hydroxymethyl-3,3′-di-O-benzyl-6-nitro-2,3,4, 5-tetrahydroxycyclohexane-carbaldehyde diphenyldithioacetal.
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    • A sample of natural, -tetrodotoxin was obtained from Sankyo Co. Ltd, Tokyo, Japan
    • A sample of natural (-)-tetrodotoxin was obtained from Sankyo Co. Ltd. (Tokyo, Japan).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.