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Volumn 7, Issue 14, 2005, Pages 2849-2852

Allocolchicinoid synthesis via direct arylation

Author keywords

[No Author keywords available]

Indexed keywords

ALLOCOLCHICINE; COLCHICINE; DRUG DERIVATIVE; HALOGENATED HYDROCARBON; PALLADIUM;

EID: 22244467723     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0505959     Document Type: Article
Times cited : (131)

References (51)
  • 24
    • 0025872899 scopus 로고
    • For examples with heterocyclic arene coupling partners, see: (a) Kozikowski, A. P.; Ma, D. Tetrahedron Lett. 1991, 32, 3317.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3317
    • Kozikowski, A.P.1    Ma, D.2
  • 26
    • 32744456433 scopus 로고    scopus 로고
    • See ref 4a
    • Examples of selective ring closure of a seven-membered-ring with nonheteroaromatic arenes are very rare. See ref 4a.
  • 28
    • 8844220501 scopus 로고    scopus 로고
    • Successful reaction with aryl chlorides has been achieved in intermolecular reactions with electron-rich zinc pyrroles and intramolecularly in the formation of five-membered rings in moderate to good yield. See: (a) Rieth, R. D.; Mankad, N. P.; Calimano, E.; Sadighi, J. P. Org. Lett. 2004, 6, 3981.
    • (2004) Org. Lett. , vol.6 , pp. 3981
    • Rieth, R.D.1    Mankad, N.P.2    Calimano, E.3    Sadighi, J.P.4
  • 36
    • 0141768464 scopus 로고    scopus 로고
    • Examples employing aryl bromides are less common. See: (a) Cuny, G. D. Tetrahedron Lett. 2003, 44, 8149.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 8149
    • Cuny, G.D.1
  • 48
    • 18844443420 scopus 로고    scopus 로고
    • Campeau, L.-C.; Thansandote, P.; Fagnou, K. Org. Lett. 2005, 7, 1857. We attribute the diminished reactivity of the IPr carbene catalyst to the enhanced steric bulk of the NHC ligand, which may be incompatible in direct arylative ring closures that produce biaryls with three ortho substituents.
    • (2005) Org. Lett. , vol.7 , pp. 1857
    • Campeau, L.-C.1    Thansandote, P.2    Fagnou, K.3
  • 51
    • 32744465600 scopus 로고    scopus 로고
    • see refs 5 and 2c
    • Allocolchicines are known to exist as a mixture of interconverting atropisomers whose equilibrium ratio is solvent dependent. For example, see refs 5 and 2c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.