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Volumn 3, Issue 4, 2001, Pages 619-621

The first total synthesis of (±)-scopadulin, an antiviral aphidicolane diterpene

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; DITERPENE; SCOPADULIN;

EID: 18044399275     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol007059v     Document Type: Article
Times cited : (13)

References (41)
  • 10
    • 0034628228 scopus 로고    scopus 로고
    • (b) Bélanger, G.; Deslongchamps, P. Org. Lett. 2000, 2, 285. For a review on other syntheses of aphidicolanes and stemodanes up to 1996, see:
    • (2000) Org. Lett. , vol.2 , pp. 285
    • Bélanger, G.1    Deslongchamps, P.2
  • 12
    • 0029088563 scopus 로고
    • For the recent total and formal synthesis of stemodane diterpenes, see: (a) Hegarty, P.; Mann, J. Tetrahedron 1995, 51, 9079.
    • (1995) Tetrahedron , vol.51 , pp. 9079
    • Hegarty, P.1    Mann, J.2
  • 27
    • 0042438148 scopus 로고    scopus 로고
    • note
    • Unlike the model study, nitrile 10 was subjected to the reaction condition without deprotection of the TMS group, which saved one step and provided a better yield.
  • 32
    • 0041435767 scopus 로고    scopus 로고
    • note
    • Due to the Lewis acidic nature of BzOTf, a number of undesired side products formed rapidly by a combination of deketalization and debenzylation and no starting material was detected.
  • 33
    • 0042438147 scopus 로고    scopus 로고
    • note
    • 15 matrix presented
  • 34
    • 0041937209 scopus 로고    scopus 로고
    • note
    • The reaction was conducted initially with MeLi to recognize the two isomers. The desired and the undesired isomers were identified by converting both the isomers to scopadulin and 16-epi-scopadulin.
  • 38
    • 0042938870 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra.
  • 40
    • 0041937208 scopus 로고    scopus 로고
    • note
    • 11 because we surmised that the highly acidic nature of the Jones reagent might cause elimination of the tertiary alcohol at C-16.
  • 41
    • 0042938869 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra from those of natural and synthetic scopadulin.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.