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Volumn 44, Issue 10, 2005, Pages 1553-1557

Novel strategy for the synthesis of the butenolide moiety of peridinin

Author keywords

Anti elimination; Butenolides; Carotenoids; Olefination; Stereoselective synthesis

Indexed keywords

BROMINE COMPOUNDS; OLEFINS; ORGANIC ACIDS; STEREOCHEMISTRY;

EID: 16244399546     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460259     Document Type: Article
Times cited : (26)

References (64)
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    • Knight, D.W.1    Pattenden, G.2
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    • c) pyrrhoxanthin, two-dimensional structure: J. E. Johansen, W. A. Svec, S. Liaaen-Jensen, F. T. Haxo, Phytochemistry 1974, 13, 2261-2271; three-dimensional structur: T. Aakermann, S. Liaaen-Jensen, Phytochemistry 1992, 31, 1779-1782;
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    • c) pyrrhoxanthin, two-dimensional structure: J. E. Johansen, W. A. Svec, S. Liaaen-Jensen, F. T. Haxo, Phytochemistry 1974, 13, 2261-2271; three-dimensional structur: T. Aakermann, S. Liaaen-Jensen, Phytochemistry 1992, 31, 1779-1782;
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    • ref. [3c]
    • γ-Alkylidenebutenolides are also part of the following carotenoids: a) peridinol: ref. [3c];
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    • c) pyrrhoxanthin: ref. [3c];
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    • ref. [3c]
    • d) pyrrhoxanthinol: ref. [3c];
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    • ref. [6g]
    • h) anhydrouriolide: ref. [6g];
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    • i) 3′-dehydrouriolide: ref. [6g];
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    • a) N. Furuichi, H. Hara, T. Osaki, H. Mori, S. Katsumura, Angew. Chem. 2002, 114, 1065-1068; Angew. Chem. Int. Ed. 2002, 41, 1023-1026;
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    • note
    • 13C NMR spectra and correct combustion analyses, except aldehyde 21, (hydroxyalkyl)butenolides 35, 4, and 5, and the unstable alkylidenebutenolides 36 and 37; all of these, however, provided correct high-resolution mass spectra.
  • 43
    • 16244385562 scopus 로고    scopus 로고
    • note
    • 2Et gave the ethyl ester/Weinreb amide analogue of 17 as an E:Z mixture (93% yield, E:Z = 59:41).
  • 45
    • 16244406496 scopus 로고    scopus 로고
    • note
    • 2Et gave all four diene stereoisomers of the ethyl ester/Weinreb amide analogue of 18 in a combined yield of 49%.
  • 56
    • 16244417108 scopus 로고    scopus 로고
    • note
    • H(B),117Sn = 71.7 Hz; A: 1-H, B: 2-H).
  • 57
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    • Dissertation, Universität Freiburg
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    • 16244375814 scopus 로고    scopus 로고
    • note
    • 4′,3′ = 11.5 Hz, 4′-H).
  • 62
    • 16244416465 scopus 로고    scopus 로고
    • note
    • 4‴,3‴ = 11.5 Hz, 4‴-H).
  • 63
    • 16244403565 scopus 로고    scopus 로고
    • note
    • 6) data see Scheme 6.
  • 64
    • 16244415475 scopus 로고    scopus 로고
    • note
    • 3 (71% yield). In the same way, when we processed the aldehyde analogue of the ester-substituted bromobutenolide 35, we could swap the steps, i.e., start with the elimination and couple with the (4S)-4-hydroxy analogue of trans-31. The detailed results will be reported in a full paper.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.