메뉴 건너뛰기




Volumn , Issue 4, 2008, Pages 501-504

Activation of enediynes via intramolecular iodoetherification

Author keywords

Bergman cyclization; Enediyne; Iodoetherification

Indexed keywords

ALIPHATIC COMPOUND; ENEDIYNE; IODINE;

EID: 40949165830     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032077     Document Type: Article
Times cited : (4)

References (31)
  • 5
    • 0003815528 scopus 로고
    • Border, D. B, Doyle, T. W, Eds, Marcel Dekker: New York
    • Enediyne Antibiotics as Antitumor Agents; Border, D. B.; Doyle, T. W., Eds.; Marcel Dekker: New York, 1995.
    • (1995) Enediyne Antibiotics as Antitumor Agents
  • 27
    • 0001380819 scopus 로고    scopus 로고
    • Myers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057. (d) Myers, A. G.; Dragovich, P. S.; Kuo, E. Y. J. Am. Chem. Soc. 1992, 114, 9369.
    • (c) Myers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057. (d) Myers, A. G.; Dragovich, P. S.; Kuo, E. Y. J. Am. Chem. Soc. 1992, 114, 9369.
  • 30
    • 40949146637 scopus 로고    scopus 로고
    • To a solution of compound 3 (150 mg, 1.03 mmol) in anhyd MeCN (10 mL, NIS (278 mg, 1.23 mmol) was added and stirred for 3 d under inert atmosphere. The reaction mixture was extracted with Et2O, washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude was purified via chromatography (SiO2, hexane-EtOAc, 30:1) to yield the desired compound 5 (34, Selected Spectral Data Compound 5: 1H NMR (200 MHz, CDCl3, δ, 3.35 (2 H, t, J, 4.0 Hz, CH2CH2O, 4.26 (2 H, t, J, 4.1 Hz, CH2CH2O, 5.64 (1 H, d, J, 8.4 Hz, ArCHCHOCH2, 6.54 (1 H, d, J, 8.4 Hz, ArCHCHOCH2, 7.28 (1 H, d, J, 8.3 Hz, ArH, 7.38 (1 H, d, J, 8.3 Hz, ArH, 13C NMR 50 MHz, CDCl3, δ, 43.02, 71.28, 100.68, 100.76, 108.71, 136.99, 138.08, 139.11
    • 2O].
  • 31
    • 40949160252 scopus 로고    scopus 로고
    • To a solution of alcohol 6 (10 mg, 0.037 mmol) in CH 2Cl2 (5 mL, Ac2O (4 μL, 0.044 mmol, Et3N (6 μL, 0.044 mmol, and DMAP (5 mol, were added at 0°C. The reaction mixture was stirred for 10 min after which it was poured into H2O and CH2Cl2. The organic layer was washed with H2O, dried, and then evaporated. The compound 6a was then isolated by column chromatography (SiO2, hexane-EtOAc, 30:1) as a white solid (98, Selected Spectral Data Compound 6a: 1H NMR (400 MHz, CDCl3, δ, 2.14 (3 H, s, CH3COOCH, 2.94, 3.50 (2 H, ABX, JAX= 4.4 Hz, JBX, 0.0 Hz, JAB, 14.8 Hz, ArCH2CHOH, 5.87 (1 H, d, J, 4.0 Hz, ArCHOHCH2, 7.28 (1 H, d, J, 8.4 Hz, ArH, 7.36 1 H, d, J, 8.0 Hz, ArH, 13
    • +].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.