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Volumn 20, Issue 9, 2014, Pages 2436-2439

Enantioselective total synthesis of dysidavarone A, a novel sesquiterpenoid quinone from the marine sponge dysidea avara

Author keywords

copper enolate; dysidavarone A; Michael addition; sesquiterpenoids; total synthesis

Indexed keywords

ADDITION REACTIONS; COPPER; SYNTHESIS (CHEMICAL);

EID: 84897617105     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201304809     Document Type: Article
Times cited : (26)

References (26)
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    • This endo-type Michael addition is quite unique in that only one example has appeared in the literature. Danishefsky eta al. reported an intramolecular Michael addition of a ketone enolate to a quinone ring for the construction of a benzo[d]anthracene core structure, see:, D. M. Gordon, S. J. Danishefsky, J. Org. Chem. 1992, 57, 7052-7055.
    • (1992) J. Org. Chem. , vol.57 , pp. 7052-7055
    • Gordon, D.M.1    Danishefsky, S.J.2
  • 8
    • 84880006043 scopus 로고    scopus 로고
    • Total synthesis of strained terpenoid natural products has been recently highlighted, see:, K. J. Hale, Org. Lett. 2013, 15, 3181-3198.
    • (2013) Org. Lett. , vol.15 , pp. 3181-3198
    • Hale, K.J.1
  • 9
    • 0001632979 scopus 로고
    • G. Stork, P. Rosen, N. Goldman, R. V. Coombs, J. Tsuji, J. Am. Chem. Soc. 1965, 87, 275-286), has been widely used as a critical step in the total synthesis of marine sesquiterpenoidquinones and hydroquinones. For examples; see
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 275-286
    • Stork, G.1    Rosen, P.2    Goldman, N.3    Coombs, R.V.4    Tsuji, J.5
  • 16
    • 35048836675 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 7458-7461
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7458-7461
  • 21
    • 0001769274 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford
    • For a review on the formation of metallic enolates, see:, H. B. Mekelburger, C. S. Wilcox, in Comprehensive Organic Synthesis Vol. 2 (Eds.:, B.a M. Trost, I. Fleming,), Pergamon, Oxford, 1991, pp.a 99-131.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 99-131
    • Mekelburger, H.B.1    Wilcox, C.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.