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Volumn 4, Issue 16, 2002, Pages 2679-2682

Stereocontrolled synthesis of 8,11-dideoxytetrodotoxin, unnatural analogue of puffer fish toxin

Author keywords

[No Author keywords available]

Indexed keywords

8,11 DIDEOXYTETRODOTOXIN; 8,11-DIDEOXYTETRODOTOXIN; DRUG DERIVATIVE; TETRODOTOXIN;

EID: 0037043491     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026177a     Document Type: Article
Times cited : (46)

References (48)
  • 25
    • 0042505791 scopus 로고
    • Ph.D. Thesis, Harvard University, Cambridge, MA
    • (f) Speslacis, J. Ph.D. Thesis, Harvard University, Cambridge, MA, 1975.
    • (1975)
    • Speslacis, J.1
  • 27
    • 0043006793 scopus 로고    scopus 로고
    • The numbering used in this paper corresponds to that of tetrodotoxin
    • The numbering used in this paper corresponds to that of tetrodotoxin.
  • 28
    • 0041504030 scopus 로고    scopus 로고
    • note
    • 7 while hydrolysis of 8 under the same conditions did not proceed. Attempted one-step conversion of 8 to 9 under forcing hydrolytic conditions failed.
  • 29
    • 0042005080 scopus 로고    scopus 로고
    • note
    • The protective group was critical not only for the further functionalization, but for final successful deprotection.
  • 32
    • 0042005078 scopus 로고    scopus 로고
    • note
    • 1H NMR).
  • 33
    • 0042505789 scopus 로고    scopus 로고
    • note
    • Determination of the configuration of C-9 is included in Supporting Information.
  • 35
    • 0042005079 scopus 로고    scopus 로고
    • note
    • The TMS group of acetylene was removed when the crude ynone was dissolved in MeOH dried over 3 Å molecular sieves.
  • 36
    • 0042005076 scopus 로고    scopus 로고
    • note
    • We found that a small amount of water drove the in situ deprotection of TMS ether and subsequent acetylation to give 14 in one pot.
  • 37
    • 0043006792 scopus 로고    scopus 로고
    • note
    • A series of these reactions were performed without purification, because of the instability of the intermediates.
  • 40
    • 0043006791 scopus 로고    scopus 로고
    • note
    • Configurations of the C-4 position of 16a and 16b were established to be S and R by coupling constants between H-4 and H-4a (0 and 4 Hz, respectively). See ref 8.
  • 41
    • 0042005077 scopus 로고    scopus 로고
    • note
    • Details will be disclosed in a full account of this study.
  • 43
    • 0042505788 scopus 로고    scopus 로고
    • note
    • Structures of the products have not been fully elucidated, because of the instability.
  • 48
    • 0041504029 scopus 로고    scopus 로고
    • note
    • 1H NMR).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.