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Volumn 3, Issue 7, 2001, Pages 975-978

Synthetic studies toward the C5-C20 domain of the azaspiracids

Author keywords

[No Author keywords available]

Indexed keywords

AZASPIRACID; FURAN DERIVATIVE; MARINE TOXIN; SOLVENT; SPIRO COMPOUND; TETRAHYDROFURAN;

EID: 0035810406     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.5555/ol015570y     Document Type: Article
Times cited : (54)

References (28)
  • 3
    • 0033580904 scopus 로고    scopus 로고
    • For a review of bis-spiroketal natural products and their syntheses see: (a) Brimble, M. A.; Farès, F. A. Tetrahedron 1999, 55, 7661.
    • (1999) Tetrahedron , vol.55 , pp. 7661
    • Brimble, M.A.1    Farès, F.A.2
  • 9
    • 0030865642 scopus 로고    scopus 로고
    • A similar acid-triggered speroketalization was employed to install the dioxaspiro[4.5]nonane system of okadaic acid: Forsyth, C. J.; Sabes, S. F.; Urbanek, R. A. J. Am. Chem. Soc. 1997, 119, 8381.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 8381
    • Forsyth, C.J.1    Sabes, S.F.2    Urbanek, R.A.3
  • 10
    • 0041789564 scopus 로고    scopus 로고
    • note
    • Numbering corresponds to that of 1-3.
  • 12
    • 0041289021 scopus 로고    scopus 로고
    • note
    • Compound 9 is commercially available from Aldrich Chemical Co., or it can be synthesized via addition of allylmagnesium bromide to acrolein.
  • 16
    • 0001646391 scopus 로고
    • Either enantiomer of 9 is available in high % ee from the enantioselective allylation of acrolein with the appropriate B-allyldiisopinocampheylborane; see: Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401.
    • (1991) J. Org. Chem. , vol.56 , pp. 401
    • Racherla, U.S.1    Brown, H.C.2
  • 19
    • 0041289020 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopic analysis. This suggests that the poor diastereoselectivity does not simply result from intramolecular directing effects of the internal diol.
  • 25
    • 85065239587 scopus 로고
    • Corey, E. J.; Weisel, L. O.; Chamberlin, A. R.; Lipshutz, B. J. Am. Chem. Soc. 1980, 102, 1439. Hicks, D. R.; Fraser-Reid, B. Synthesis 1974, 203.
    • (1974) Synthesis , pp. 203
    • Hicks, D.R.1    Fraser-Reid, B.2
  • 26
    • 0041288990 scopus 로고    scopus 로고
    • note
    • For convenience on a multigram scale, the mixture of 8 and 12 was typically used directly in the THF-rinng formation step, at which stage diol 7 was readily separated from its C19 epimer by column chromatography.
  • 27
    • 0041789538 scopus 로고    scopus 로고
    • note
    • 2
  • 28
    • 0041288991 scopus 로고    scopus 로고
    • note
    • 3CN, 24-48 h).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.