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Volumn 44, Issue 5, 2005, Pages 765-769

Spirocycloisomerization of tethered alkylidene glycocyamidines: Synthesis of a base template common to the palau'amine family of alkaloids

Author keywords

Cyclization; Guanidines; Heterocycles; Natural products; Total synthesis

Indexed keywords

ISOMERIZATION; SYNTHESIS (CHEMICAL);

EID: 13444252897     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462069     Document Type: Article
Times cited : (71)

References (27)
  • 9
    • 2942673078 scopus 로고    scopus 로고
    • d) P. S. Baran, D. P. O'Malley, A. L. Zografos, Angew. Chem. 2004, 116, 2728-2731; Angew. Chem. Int. Ed. 2004, 43, 2674-2677.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2674-2677
  • 12
    • 4544360320 scopus 로고    scopus 로고
    • As 1-3 are currently inaccessible, there has been considerable attention paid to the synthetic problem; for a review see reference [4b]. More recent contributions include: a) J. D. Katz, L. E. Overman, Tetrahedron 2004, 60, 9559-9568;
    • (2004) Tetrahedron , vol.60 , pp. 9559-9568
    • Katz, J.D.1    Overman, L.E.2
  • 16
    • 0009507603 scopus 로고
    • Glycocyamidine nomenclature refers to cyclic anhydrides of α-guanidino carboxylic acids; the prototype is derived from glycine: C. Lempert, Chem. Rev. 1959, 59, 667-736; the equivalent IUPAC designation is 2-amino-1H-5-imidazolone.
    • (1959) Chem. Rev. , vol.59 , pp. 667-736
    • Lempert, C.1
  • 23
    • 13444262068 scopus 로고    scopus 로고
    • note
    • See Supporting Information.
  • 24
    • 13444306346 scopus 로고    scopus 로고
    • note
    • 2OH provides vicinal bifunctionalization products in low yields, analogous to those generated from monomer 13 (Scheme 3) under similar conditions.
  • 25
    • 13444263448 scopus 로고    scopus 로고
    • Crystallographic data (excluding structure factors) for 17 and (Z)-24 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 250890 and CCDC 250891. 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 CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
  • 26
    • 13444291251 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of California, Irvine, 2000, UMI no. 9950654
    • W. C. Trenkle, Ph.D. Thesis, University of California, Irvine, 2000, UMI no. 9950654.
    • Trenkle, W.C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.