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Volumn 7, Issue 20, 2005, Pages 4317-4320

Total synthesis of (-)-colchicine via a Rh-triggered cycloaddition cascade

Author keywords

[No Author keywords available]

Indexed keywords

COLCHICINE; RHODIUM;

EID: 26444437208     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051316k     Document Type: Article
Times cited : (103)

References (34)
  • 1
    • 77957769724 scopus 로고
    • Brossi, A., Cordell, G. A., Eds.; Academic Press: San Diego
    • (a) Boyé, O.; Brossi, A. In The Alkaloids; Brossi, A., Cordell, G. A., Eds.; Academic Press: San Diego, 1992; Vol. 41, p 125.
    • (1992) The Alkaloids , vol.41 , pp. 125
    • Boyé, O.1    Brossi, A.2
  • 2
    • 26444442113 scopus 로고    scopus 로고
    • Cordell, G. A., Ed.; Academic Press: San Diego, Chapter 5
    • (b) Le Hello, C. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 2000; Vol. 53, Chapter 5.
    • (2000) The Alkaloids , vol.53
    • Le Hello, C.1
  • 8
    • 0000541751 scopus 로고    scopus 로고
    • Most recent colchicine syntheses: (a) Banwell, M. G. Pure Appl. Chem. 1996, 68, 539.
    • (1996) Pure Appl. Chem. , vol.68 , pp. 539
    • Banwell, M.G.1
  • 12
    • 0036322149 scopus 로고    scopus 로고
    • The intention to apply the same strategy for a colchicine total synthesis was put forward after our first disclosure: McMills, M.; Wright, D. L.; Weekly, R. M. Synth. Commun. 2002, 32, 2417.
    • (2002) Synth. Commun. , vol.32 , pp. 2417
    • McMills, M.1    Wright, D.L.2    Weekly, R.M.3
  • 15
    • 26444593090 scopus 로고    scopus 로고
    • note
    • Attempts to utilize an aryllithium species derived from 9 by treatment with BuLi failed due to deprotonation at the propargylic stereocenter (intramolecular proton transfer).
  • 17
    • 26444456730 scopus 로고    scopus 로고
    • note
    • Diacel Chiralpak AD-H, hexane/i-PrOH = 9:1.
  • 21
    • 33751391278 scopus 로고
    • 4, PhH, rt), compound 11 only afforded a dihydropyranone side-product resulting from 1,4 H-shift of the reactive intermediate 3. A similar side-product has been observed by Padwa in the reaction of a simple model compound. See: Padwa, A.; Hornbuckle, S. F.; Fryxell, G. E.; Zhang, Z. J. J. Org. Chem. 1992, 57, 5747.
    • (1992) J. Org. Chem. , vol.57 , pp. 5747
    • Padwa, A.1    Hornbuckle, S.F.2    Fryxell, G.E.3    Zhang, Z.J.4
  • 24
    • 0003075009 scopus 로고    scopus 로고
    • For a review on ring opening reactions in oxabicyclic ring systems, see: (c) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 1.
    • (1997) Top. Curr. Chem. , vol.190 , pp. 1
    • Chiu, P.1    Lautens, M.2
  • 25
    • 26444571006 scopus 로고    scopus 로고
    • note
    • The cleavage of the benzylic C-O bond should also be stereoelectronically assisted as the oxa-bridge is aligned with the π-system of the aromatic ring.
  • 26
    • 26444435451 scopus 로고    scopus 로고
    • note
    • Compound 16 also proved to be rather sensitive toward decomposition and was usually directly further oxidized to the tropolone 23 (Scheme 4).
  • 34
    • 26444517890 scopus 로고    scopus 로고
    • see ref 1a
    • -1. For details, see ref 1a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.