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Volumn 65, Issue 19, 2000, Pages 5910-5916

First total synthesis of Aspinolide B, a new pentaketide produced by Aspergillus ochraceus

Author keywords

[No Author keywords available]

Indexed keywords

ASPINOLIDE B; UNCLASSIFIED DRUG;

EID: 0034703199     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000327i     Document Type: Article
Times cited : (42)

References (31)
  • 18
    • 0028316585 scopus 로고
    • 3SnCl 78% (Cabezas, J. A.; Oehlschlager, A. C. Synthesis 1994, 432); ethynyl(tributyl)tin, n-BuSnH, AIBN 96% (Corey, E. J.; Wollenberg, R. H. J. Am. Chem. Soc. 1974, 96, 5581).
    • (1994) Synthesis , pp. 432
    • Cabezas, J.A.1    Oehlschlager, A.C.2
  • 19
    • 33847805703 scopus 로고
    • 3SnCl 78% (Cabezas, J. A.; Oehlschlager, A. C. Synthesis 1994, 432); ethynyl(tributyl)tin, n-BuSnH, AIBN 96% (Corey, E. J.; Wollenberg, R. H. J. Am. Chem. Soc. 1974, 96, 5581).
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 5581
    • Corey, E.J.1    Wollenberg, R.H.2
  • 20
    • 0342907668 scopus 로고    scopus 로고
    • note
    • 3, MeOH.
  • 27
    • 0343342765 scopus 로고    scopus 로고
    • note
    • 2 purchased from Merck Schuchardt or Aldrich (>99.9%) and dried at 1 mmHg and 250°C for 4 h immediately prior to use.
  • 28
    • 0342473313 scopus 로고    scopus 로고
    • note
    • 1H NMR data of aspinolide B which displays H8 at 4.94 ppm as a double dublet (J = 9.0, 8.0 Hz), characteristic of trans diaxial orientation. In comparison, H8 in 24a (δ 3.83 ppm) appears as double triplet (J = 8.5, 8.5, 5.0 Hz) while in 24b (δ 4.30 ppm) as a singlet.
  • 29
    • 0342907667 scopus 로고    scopus 로고
    • note
    • Mitsunobu reaction carried out with crotonic acid instead of p-NBA was unsucessfull.
  • 30
    • 0342473314 scopus 로고    scopus 로고
    • note
    • D -19.1 (c 1.0, MeOH)).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.