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Volumn 9, Issue 12, 2007, Pages 2293-2295

Synthesis of the tricyclic core of colchicine via a dienyne tandem ring-closing metathesis reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; COLCHICINE;

EID: 34250816255     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070708j     Document Type: Article
Times cited : (32)

References (33)
  • 1
    • 0025483995 scopus 로고
    • For a summary of the synthesis and biological activity of colchicine and allo congeners see:, and references therein
    • For a summary of the synthesis and biological activity of colchicine and allo congeners see: Brossi, A. J. Med. Chem. 1990, 33, 2311 and references therein.
    • (1990) J. Med. Chem , vol.33 , pp. 2311
    • Brossi, A.1
  • 2
    • 33847776291 scopus 로고    scopus 로고
    • For a review on microtubule-targeted drugs see
    • For a review on microtubule-targeted drugs see: Jordan, M. A.; Wilson, L. Nat. Rev. Cancer 2004, 59, 163.
    • (2004) Nat. Rev. Cancer , vol.59 , pp. 163
    • Jordan, M.A.1    Wilson, L.2
  • 3
    • 4544286643 scopus 로고    scopus 로고
    • For a recent review on the total syntheses of colchicines see
    • For a recent review on the total syntheses of colchicines see: Graening, T.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2004, 43, 3230.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 3230
    • Graening, T.1    Schmalz, H.-G.2
  • 8
    • 0001117364 scopus 로고    scopus 로고
    • For selected examples of synthesis of polycyclic systems by tandem metathesis of dienynes, see: a
    • For selected examples of synthesis of polycyclic systems by tandem metathesis of dienynes, see: (a) Zuercher, W. J.; Scholl, M.; Grubbs., R. H. J. Org. Chem. 1998, 63, 4291.
    • (1998) J. Org. Chem , vol.63 , pp. 4291
    • Zuercher, W.J.1    Scholl, M.2    Grubbs, R.H.3
  • 20
    • 34250846774 scopus 로고    scopus 로고
    • Attempts to construct fused 7,7-bicyclic compounds from acyclic dienynes by tandem RCM failed (see ref. 7e).
    • Attempts to construct fused 7,7-bicyclic compounds from acyclic dienynes by tandem RCM failed (see ref. 7e).
  • 23
    • 34250802975 scopus 로고    scopus 로고
    • 6-Bromo-2-methyl-hex-2-ene was prepared in three steps from y-butyrolactone: reduction with DIBAH followed by Wittig reaction and bromation of the resulting primary alcohol. For details see Supporting Information.
    • 6-Bromo-2-methyl-hex-2-ene was prepared in three steps from y-butyrolactone: reduction with DIBAH followed by Wittig reaction and bromation of the resulting primary alcohol. For details see Supporting Information.
  • 24
    • 34250847380 scopus 로고    scopus 로고
    • To get the indicated yield, it is important to observe the following work up. After the completion of the reaction, silica gel was added at -70 °C, and the reaction mixture was allowed to warm to 0°C. The crude aldehyde was isolated by filtration and was purified by flash column chromatography. Otherwise, treatment of the reaction mixture with Rochelle's salt (potassium and sodium tartrate solution) resulted in the complete degradation of the product.
    • To get the indicated yield, it is important to observe the following work up. After the completion of the reaction, silica gel was added at -70 °C, and the reaction mixture was allowed to warm to 0°C. The crude aldehyde was isolated by filtration and was purified by flash column chromatography. Otherwise, treatment of the reaction mixture with Rochelle's salt (potassium and sodium tartrate solution) resulted in the complete degradation of the product.
  • 30
    • 34250794210 scopus 로고    scopus 로고
    • Wenkert, E.; Kim, H.-S. In Studies in Natural Products Chemistry; Atta-ur-Rhaman, Ed.; Elsevier: Amsterdam, The Netherlands, 1989; 3, Part B, p 287.
    • Wenkert, E.; Kim, H.-S. In Studies in Natural Products Chemistry; Atta-ur-Rhaman, Ed.; Elsevier: Amsterdam, The Netherlands, 1989; Vol. 3, Part B, p 287.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.