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Volumn 9, Issue 4, 2011, Pages 998-1000

Synthesis of the (-)-TAN-2483B ring system via a D-mannose-derived cyclopropane

Author keywords

[No Author keywords available]

Indexed keywords

FUNGAL METABOLITES; RING SYSTEMS;

EID: 79551665529     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00851f     Document Type: Article
Times cited : (11)

References (17)
  • 6
    • 79551678168 scopus 로고    scopus 로고
    • Jpn. Patent 10287679, Chem. Abstr. 1999, 130, 3122e
    • K. Hayashi, M. Takizawa, and K. Noguchi, Jpn. Patent 10287679, 1998; Chem. Abstr. 1999, 130, 3122e
    • (1998)
    • Hayashi, K.1    Takizawa, M.2    Noguchi, K.3
  • 10
    • 4043130151 scopus 로고    scopus 로고
    • A multi-component approach to the furo[3,4-b]pyran-5-one ring system has also been reported:
    • X. Gao B. B. Snider J. Org. Chem. 2004 69 5517 5527
    • (2004) J. Org. Chem. , vol.69 , pp. 5517-5527
    • Gao, X.1    Snider, B.B.2
  • 17
    • 75749136914 scopus 로고    scopus 로고
    • Molecular mechanics calculations (see Supporting Information) indicate that the distance between H-2 and H-7a in the undesired epimer, 7a-epi-6, would be ca. 2.38 Å, so a strong nOe signal would be expected. The absence of an nOe implies that the desired isomer, 6, is formed. This assignment is corroborated by nOe enhancements between H-7a and protons on the top face as drawn: H5′, an aromatic proton of the benzyl group, and the proton attached to C-7 that does not interact with H-2 (the other H-7 displays a weaker nOe with H-7a and a distinct correlation with H-2)
    • R. J. Hewitt J. E. Harvey J. Org. Chem. 2010 75 955 958
    • (2010) J. Org. Chem. , vol.75 , pp. 955-958
    • Hewitt, R.J.1    Harvey, J.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.