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Volumn 11, Issue 24, 2009, Pages 5658-5661

Asymmetrie construction of rings A - D of Daphnicyclidin-type alkaloids

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; DAPHNIPAXININ;

EID: 72849144727     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902373m     Document Type: Article
Times cited : (70)

References (26)
  • 2
    • 70249089612 scopus 로고    scopus 로고
    • and other reviews cited therein
    • Kobayashi, J.; Kubota, T. Nat. Prod Rep. 2009, 26, 936-962, and other reviews cited therein.
    • (2009) Nat. Prod Rep. , vol.26 , pp. 936-962
    • Kobayashi, J.1    Kubota, T.2
  • 3
    • 72849136215 scopus 로고    scopus 로고
    • Alkaloids 1, 2 and 4 have been characterized by single crystal X-ray analysis: (a) Reference 2
    • Alkaloids 1, 2 and 4 have been characterized by single crystal X-ray analysis: (a) Reference 2.
  • 7
    • 72849134798 scopus 로고    scopus 로고
    • For example, daphnipaxinin (3) and oldhamine A (4) were isolated in 0.00024 and 0.00007%, respectively, from their dried plant sources
    • For example, daphnipaxinin (3) and oldhamine A (4) were isolated in 0.00024 and 0.00007%, respectively, from their dried plant sources.
  • 8
    • 67650493974 scopus 로고    scopus 로고
    • For a recent brief review and leading references, see Overman, L. E. Tetrahedron 2009, 65, 6432-6446.
    • (2009) Tetrahedron , vol.65 , pp. 6432-6446
    • Overman, L.E.1
  • 9
    • 65249190992 scopus 로고    scopus 로고
    • An enantiocontrolled route to a BCD ring fragment of daphnicyclidin A was described recently, see: Ikeda, S.; Shibuya, M.; Kanoh, N.; Iwabuchi, Y. Org. Lett. 2009, 11, 1833-1836.
    • (2009) Org. Lett. , vol.11 , pp. 1833-1836
    • Ikeda, S.1    Shibuya, M.2    Kanoh, N.3    Iwabuchi, Y.4
  • 11
    • 72849136476 scopus 로고    scopus 로고
    • Ph.D. Dissertation, University of California, Irvine
    • Kowalski, M. D. Ph.D. Dissertation, University of California, Irvine, 2008.
    • (2008)
    • Kowalski, M.D.1
  • 13
    • 72849152179 scopus 로고    scopus 로고
    • 10 configuration of the major alcohol epimer was confirmed by X-ray analysis of a subsequent product
    • 10 configuration of the major alcohol epimer was confirmed by X-ray analysis of a subsequent product.
  • 17
    • 72849126039 scopus 로고    scopus 로고
    • A minor amount of a third stereoisomeric adduct that derives from the inseparable minor alcohol epimer of intermediate 13 was also produced
    • A minor amount of a third stereoisomeric adduct that derives from the inseparable minor alcohol epimer of intermediate 13 was also produced.
  • 21
    • 57149084689 scopus 로고    scopus 로고
    • We employed a simpler procedure for preparing this reagent (see Supporting Information); for a related procedure for preparing a cerium acetylide, see: (b) Trost, B. M.; Waser, J.; Meyer, A. J. Am. Chem. Soc. 2008, 130, 16424-16434.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 16424-16434
    • Trost, B.M.1    Waser, J.2    Meyer, A.3
  • 22
    • 72849152446 scopus 로고    scopus 로고
    • note
    • Aza-Cope-Mannich product 22a was elaborated to a tricyclic pyrrolidinium salt by cleavage of the TBDPS group and intramolecular quaternization by the sequence illustrated in Schemes 4 and 5; see Supporting Information for details. Single crystal X-ray analysis of this derivative confirmed the relative and absolute configuration of 22a. Crystallographic data for this compound were deposited with the Cambridge Crystallographic Data Centre: CCDC 751136.
  • 23
    • 0035954898 scopus 로고    scopus 로고
    • For a pertinent example where this reaction also failed to form a seven-membered ring, see: Dudley, G. B.; Danishefsky, S. J. Org. Lett. 2001, 3, 2399-2402.
    • (2001) J. Org. Lett. , vol.3 , pp. 2399-2402
    • Dudley, G.B.1    Danishefsky, S.2
  • 24
    • 0037486826 scopus 로고    scopus 로고
    • For a review, see: Fürstner, A. Chem. Rev. 1999, 99, 991-1045.
    • (1999) Chem. Rev. , vol.99 , pp. 991-1045
    • Fürstner, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.