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Volumn 64, Issue 19, 2008, Pages 4233-4245

Facile formation of tetrahydrofurans with multiple chiral centers using double iodoetherification of σ-symmetric diene acetals: short asymmetric total synthesis of rubrenolide and rubrynolide

Author keywords

Acyclic diene acetal; Asymmetric synthesis; Intramolecular haloetherification; Rubrenolide; Rubrynolide

Indexed keywords

ACETAL DERIVATIVE; ALKADIENE; HYDROXYL GROUP; RUBRENOLIDE; RUBRYNOLIDE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 41549159197     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.088     Document Type: Article
Times cited : (18)

References (44)
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    • Diallylmethyl aldehyde 4c was prepared from the known diallyl ester 17 (. {A figure is presented}
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    • ) in two steps: (1) reduction of ester with DiBAL-H and (2) PDC oxidation. {A figure is presented}
    • Snider B.B., and Smith R.B. Tetrahedron 58 (2002) 25-34 ) in two steps: (1) reduction of ester with DiBAL-H and (2) PDC oxidation. {A figure is presented}
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    • note
    • CCDC-244868 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; or e-mail: deposit@ccdc.cam.ac.uk.
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    • For the radical reduction using VA-061 in water including this transformation, see:
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    • Taylor S.K., Hopkins J.A., Spangenberg K.A., McMillen D.W., and Grutzner J.B. J. Org. Chem. 56 (1991) 5951-5955 Although wrong stereochemical structure of rubrenolide was originally proposed, the correct one was reported by Zwanenburg et al. (see Ref. 12)
    • (1991) J. Org. Chem. , vol.56 , pp. 5951-5955
    • Taylor, S.K.1    Hopkins, J.A.2    Spangenberg, K.A.3    McMillen, D.W.4    Grutzner, J.B.5
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    • For asymmetric total synthesis, see:
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    • note
    • 2O was better for large-scale reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.