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Synlett
Volumn , Issue 12, 2007, Pages 1940-1944
A general synthesis of phenanthridinone alkaloids
Author keywords

Diels Alder cycloadditions; Regioselectivity; Stereoselectivity
Indexed keywords

3 BROMO 2(H)PYRAN 2 ONE; 7 DEOXYPANCRATISTATINE; ALKALOID DERIVATIVE; LACTONE DERIVATIVE; LYCORICIDINE; NARCICLASINE; PANCRATISTATINE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;
EID: 34547615778     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984540     Document Type: Article
Times cited : (18)
References (45)
  • 1
    • 34547626030 scopus 로고    scopus 로고
    • Previous address: Department of Chemistry, King's College London, Strand, London WC2R 2LS, UK.
    • Previous address: Department of Chemistry, King's College London, Strand, London WC2R 2LS, UK.
  • 2
    • 14844285469 scopus 로고    scopus 로고
    • Amaryllidaceae alkaloids as a structural class are regularly reviewed. For example, see: Jin, Z
    • Amaryllidaceae alkaloids as a structural class are regularly reviewed. For example, see: Jin, Z. Nat. Prod. Rep. 2005, 22, 111.
    • (2005) Nat. Prod. Rep , vol.22 , pp. 111
  • 10
  • 11
    • 14644422595 scopus 로고    scopus 로고
    • 365. More recent examples include
    • (c) Rinner, U.; Hudlicky, T. Synlett 2005, 365. More recent examples include:
    • (2005) Synlett
    • Rinner, U.1    Hudlicky, T.2
  • 37
    • 34547626361 scopus 로고    scopus 로고
    • Compound 7 A sealed pressure tube (Aldrich Chemical Co Cat No Z18, 109-9) was charged with 3-bromo-2 (H)-pyran-2-one (617 mg, 3.53 mmol, 3,4-dimethoxystyrene (2.5 g, 15.2 mmol, a few crystals of 2,6-di-tert- butyl-4-methylphenol (antipolymerization agent, and a small magnetic stirrer bar. The pressure tube was sealed and heated at 80°C for 5 d. Removal of all volatile materials followed by silica gel chromatography using 20-40% v/v EtOAc in PE afforded the endo-isomer (1.16 g, 97, 1H NMR: δ, 6.80 (1 H, aromatic, 6.72 (2 H, aromatic, 6.67 (dd, 1 H, J 1,7, 5.2 Hz, J7,8, 7.8 Hz, H-7, 6.46 (dm, 1 H, J7,8, 7.8 Hz, H-8, 5.39 (m, 1 H, H-1, 3.87 (s, 3 H, OCH3, 3.86 (s, 3 H, OCH3, 3.33 (ddd, 1 H, J 5,8, 0.9 Hz, J5,6endo, 4.5 Hz, J 5,6exo, 9.7 Hz, H-5, 2.95 ddd, 1 H, J1,6exo, 4.2
    • 4Na: 363.00255; found: 363.00247.
  • 42
    • 34547646288 scopus 로고    scopus 로고
    • Compound 8 A round-bottomed flask was charged with a solution of compound 7 (339 mg, 1 mmol) in anhyd MeOH (15 mL) and Pd/C (10% w/w, 60 mg, The reaction mixture was stirred at r.t. under H2 atmosphere for 45 h. The mixture was filtered through Celite® and the solid residue washed with EtOAc. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using 40% EtOAc in PE to give compound 8 (272 mg, 93, >H NMR: δ, 6.76 (3 H, aromatic, 4.30 (m, 1 H, H-4, 3.86 (s, 3 H, OCH3, 3.85 (s, 3 H, OCH3, 3.45 (s, 3 H, CO2CH3, 3.38 (dt, 1 H, J1,2, J2,3a, 4.3 Hz, J2,3e, 12.1 Hz, H-2, 2.91 (q, 1 H, J, 4.5 Hz, H-1, 2.61 (ddd; 1 H, J3e,4, 2.9 Hz, J2,3e, 12.0 Hz, J3e,3a, 13.5 Hz, H-3e, 2.20 tdd, 1 H, J1,6e, 4.0 Hz, J
    • 5Na: 317.13594; found: 317.13557.
  • 44
    • 34547615309 scopus 로고    scopus 로고
    • Compound 10 DPPA (0.2 mL, 0.94 mmol) was added to a stirred solution of compound 8 (210 mg, 0.75 mmol) and Et3N (0.2 mL, 1.5 mmol) in anhyd benzene (20 mL) at 0°C. After 30 min, the solution was brought to r.t. and then after 2 h was set to reflux for 45 h. Solvent was removed and the residue was dissolved in CH2Cl2 (3 mL, This was added to a stirred suspension of AlCl3 in CH 2Cl2 (5 mL) at 0°C. After 30 min, the solution was brought to r.t. and was stirred for 24 h. The reaction mixture was poured into H2O and was extracted with EtOAc (3 x 20 mL, The combined organic extracts were washed with aq NaHCO3 and dried over Na 2SO4. Evaporation of solvent and silica gel chromatography (20-60% v/v EtOAc in PE) afforded compound 10 as a yellow gum (49 mg, 24, 1H NMR: δ, 6.61 (s, 1 H, aromatic, 6.63 (s, 1 H, aromatic, 4.18 m, 1 H, H-4, 3.8
    • 4Na: 300.12118; found: 300.1212.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.