메뉴 건너뛰기




Volumn 14, Issue 9, 2012, Pages 2234-2237

Semipinacol rearrangement of cis-fused β-lactam diols into keto-bridged bicyclic lactams

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AZABICYCLO DERIVATIVE; BETA LACTAM;

EID: 84860617809     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300605y     Document Type: Article
Times cited : (32)

References (42)
  • 1
    • 67651052961 scopus 로고    scopus 로고
    • Securinega alkaloids
    • Securinega alkaloids: Weinreb, S. Nat. Prod. Rep. 2009, 26, 758-775
    • (2009) Nat. Prod. Rep. , vol.26 , pp. 758-775
    • Weinreb, S.1
  • 12
    • 0345225165 scopus 로고
    • The first total synthesis of peduncularine exploits a keto-bridged bicyclic lactam as a key intermediate
    • The first total synthesis of peduncularine exploits a keto-bridged bicyclic lactam as a key intermediate: Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. J. Am. Chem. Soc. 1989, 111, 2588-2595
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2588-2595
    • Klaver, W.J.1    Hiemstra, H.2    Speckamp, W.N.3
  • 18
    • 80755176872 scopus 로고    scopus 로고
    • For a review of the semipinacol rearrangement, see
    • For a review of the semipinacol rearrangement, see: Song, Z.-L.; Fan, C.-A.; Tu, Y.-Q. Chem. Rev. 2011, 111, 7523-7556
    • (2011) Chem. Rev. , vol.111 , pp. 7523-7556
    • Song, Z.-L.1    Fan, C.-A.2    Tu, Y.-Q.3
  • 19
    • 0035898786 scopus 로고    scopus 로고
    • A related rearrangement in the all carbocyclic [4.2.0]-ring system is hampered by the instability of the bridged 1,3-dicarbonyl product
    • A related rearrangement in the all carbocyclic [4.2.0]-ring system is hampered by the instability of the bridged 1,3-dicarbonyl product: Blanchard, A. N.; Burnell, D. J. Tetrahedron Lett. 2001, 42, 4779-4781
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4779-4781
    • Blanchard, A.N.1    Burnell, D.J.2
  • 20
    • 36849034419 scopus 로고    scopus 로고
    • For a review on the synthetic utility of β-lactams, see
    • For a review on the synthetic utility of β-lactams, see: Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437-4492
    • (2007) Chem. Rev. , vol.107 , pp. 4437-4492
    • Alcaide, B.1    Almendros, P.2    Aragoncillo, C.3
  • 29
    • 84860619607 scopus 로고    scopus 로고
    • CCDC 866295 (1b hydrate), CCDC 866296 (4b), CCDC 866297 (9b), CCDC 866298 (10b), and CCDC 869870 (13) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • CCDC 866295 (1b hydrate), CCDC 866296 (4b), CCDC 866297 (9b), CCDC 866298 (10b), and CCDC 869870 (13) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 31
    • 53849137698 scopus 로고    scopus 로고
    • We have previously shown that thermal elimination of dithiocarbamate 3a gives the nonconjugated alkene 5a in 79% yield
    • We have previously shown that thermal elimination of dithiocarbamate 3a gives the nonconjugated alkene 5a in 79% yield: Ahmed, S.; Baker, L. A.; Grainger, R. S.; Innocenti, P.; Quevedo, C. E. J. Org. Chem. 2008, 73, 8116-8119
    • (2008) J. Org. Chem. , vol.73 , pp. 8116-8119
    • Ahmed, S.1    Baker, L.A.2    Grainger, R.S.3    Innocenti, P.4    Quevedo, C.E.5
  • 41
    • 0021915012 scopus 로고
    • For an alternative approach to structures such as 14 based on palladium catalyzed carbonylation of 2-bromoallylamines, see
    • For an alternative approach to structures such as 14 based on palladium catalyzed carbonylation of 2-bromoallylamines, see: Mori, M.; Chiba, K.; Okita, M.; Kayo, I.; Ban, Y. Tetrahedron 1985, 41, 375-385
    • (1985) Tetrahedron , vol.41 , pp. 375-385
    • Mori, M.1    Chiba, K.2    Okita, M.3    Kayo, I.4    Ban, Y.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.