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Volumn , Issue 18, 2009, Pages 2997-2999

Total synthesis of horsfiline: A palladium-catalyzed domino Heck-cyanation strategy

Author keywords

Cyanation; Domino reaction; Heck; Horsfiline; Oxindole; Palladium

Indexed keywords

OXINDOLE; PALLADIUM; PYRROLIDINE DERIVATIVE;

EID: 72049085540     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218004     Document Type: Article
Times cited : (41)

References (59)
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    • 7044235263 scopus 로고    scopus 로고
    • For general reviews on the domino process
    • For general reviews on the domino process, see:, Tietze L F., Chem. Rev. 1996 96 115
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    • Tietze, L.F.1
  • 40
    • 43549120314 scopus 로고    scopus 로고
    • For a general review on palladium-catalyzed cross-coupling involving metal cyanides, see
    • Cheng Y.-N, Duan Z, Yu L, Li Z, Zhu Y, Wu Y, Org. Lett. 2008 10 901 For a general review on palladium-catalyzed cross-coupling involving metal cyanides, see:
    • (2008) Org. Lett. , vol.10 , pp. 901
    • Cheng, Y.-N.1    Duan, Z.2    Yu, L.3    Li, Z.4    Zhu, Y.5    Wu, Y.6
  • 50
    • 72049092852 scopus 로고    scopus 로고
    • note
    • Experimental Procedure: To a degassed solution of iodoanilide 14 (1.90 g, 3.29 mmol, 1.0 equiv) in DMF (16mL) were added K4Fe(CN)6-3H2O (306.0 mg, 0.72 mmol, 0.22 equiv), Na2CO3 (350.0 mg, 3.30 mmol, 1.0 equiv) and Pd(OAc)2 (22.0 mg, 0.1 mmol, 0.03 equiv). After being stirred at 120 °C under an argon atmosphere for 3 h, the reaction mixture was quenched with H2O and extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (SiO2, heptane-EtOAc, 95:5 →90:10) to give the corresponding oxindole 15 (0.94g, 60%) as a light orange solid. Compound 15: 1H NMR (500 MHz, CDCl3): d = 7.06 (d, J = 2.6 Hz, 1 H), 7.02 (d, J = 8.6 Hz, 1 H), 6.88 (dd, J = 8.6, 2.6 Hz, 1 H), 5.17 (d, J = 11.0 Hz, 1 H), 5.11 (d, J = 11.0 Hz, 1 H), 3.92 (d, J = 9.7 Hz, 1 H), 3.80 (s, 3 H), 3.73 (d, J = 9.7 Hz, 1 H), 3.62-3.51 (m, 2 H), 3.02 (d, J = 16.7 Hz, 1 H), 2.79 (d, J = 16.7 Hz, 1 H), 0.92 (t, J = 8.2 Hz, 2 H), 0.84 (s, 9 H), 0.00 (s, 3 H), -0.01 (s, 3 H), -0.03 (s, 9 H). 13C NMR (75 MHz, CDCl3): d = 175.4, 156.4, 135.4, 129.1, 116.2, 114.3, 111.2, 110.6, 69.9, 66.5, 66.1, 55.8, 51.9, 25.7, 21.7, 18.1, 17.7, -1.4, -5.6, -5.7. HRMS (ES+): m/z [M + Na]+ calcd for C24H40N2O4Si2Na: 499.2424; found: 499.2415.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.