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Volumn 8, Issue 18, 2006, Pages 3943-3946

Synthetic study of azaspiracid-1: Synthesis of the EFGHI-ring fragment

Author keywords

[No Author keywords available]

Indexed keywords

AZASPIRACID; MARINE TOXIN; SPIRO COMPOUND;

EID: 33748941250     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0613766     Document Type: Article
Times cited : (16)

References (43)
  • 7
    • 9144242989 scopus 로고    scopus 로고
    • For the whole story for the structural revision of 1, see: (a) Freemantle, M. Chem. Eng. News 2004, 82, 27.
    • (2004) Chem. Eng. News , vol.82 , pp. 27
    • Freemantle, M.1
  • 15
    • 0034736335 scopus 로고    scopus 로고
    • For synthetic studies on the E-, F-, G-, H-, and/or 1-ring domain of 1, see: (a) Carter, R. G.; Weldon, D. J. Org. Lett. 2000, 2, 3913.
    • (2000) Org. Lett. , vol.2 , pp. 3913
    • Carter, R.G.1    Weldon, D.J.2
  • 27
    • 33748927373 scopus 로고    scopus 로고
    • note
    • The stereochemistry of these products was determined by the modified Mosher ester analysis of undesired (R)-8, which was obtained by recrystallization.
  • 32
    • 33748947559 scopus 로고    scopus 로고
    • Prepared from 12 in 54% yield over five steps
    • Prepared from 12 in 54% yield over five steps.
  • 33
    • 33748937414 scopus 로고    scopus 로고
    • note
    • The stereoselectivity observed in the spiroaminal formation was unexpected but was reasonably explained by calculation at the MMFF94S force field. The details will be reported in the full account of this work.
  • 38
    • 0026687198 scopus 로고
    • An alkyl carbamate protecting group can be generally removed with various nucleophiles; see: (a) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5959
    • Tius, M.A.1    Kerr, M.A.2
  • 42
    • 33748924220 scopus 로고    scopus 로고
    • note
    • The allylic stannane 19 was prepared from 2-bromo-3-trimethylsilylpropene in 37% yield over nine steps. See the Supporting Information. The details will be given in the full account of this work.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.