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Volumn 36, Issue 5, 2007, Pages 654-655

Facile synthesis of (-)-ascochlorin using palladium-catalyzed three component coupling reaction

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EID: 34250171154 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2007.654 Document Type: Article

Times cited : (1)

References (17)

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15
- 34250168028
- Preparation of 5 as a typical procedure for the palladium-catalyzed three component coupling reactions in Table 1: A mixture of 3,5-dimethoxy-4-iodotoluene (3, 55.6 mg, 0.200 mmol, sodium p-toluenesulfinate (78.4 mg, 0.440 mmol, sodium hydrogen carbonate (26.2 mg, 0.312 mmol, tetra-n-butylammonium iodide (77.6 mg, 0.210 mmol, Pd2(dba)3CHCl3 (10.4 mg, 5 mol , isoprene (0.4 mL) in DMSO (0.606 mL) was stirred at 80°C for 96 h in Pyrex tube. The mixture was quenched with NH4Cl aq. The organic layer was extracted with dichloromethane, washed with brine, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo. The residue was chromatogaraphed on silica gel (10% ethyl acetate in hexane) to give the product 6 as a yellow oil (50.7 mg, 68, 1H NMR (400 MHz CDCl 3) δ 1.90 (s, 3H, CH3, 2.31 (s, 3H, CH 3, 2.33 s, 3H, CH3
- + 375.1552, found 375.1636.

17
- 34250209976
- Ascochlorin (1, mp 172-174°C (lit:2b 172-173°C, α]D25, 30.7 (c 0.69, MeOH, lit:2b [α]D25, 31 (c 0.99, MeOH, 1H NMR (400 MHz, CDCl3) δ 0.69 (s, 3H, CH3, 0.80-0.84 (m, 6H, 1.60-1.67 (m, 1H, 1.89-1.96 (m, 2H, 1.92 (s, 3H, CH3, 2.33-2.46 (m, 3H, 2.60 (s, 3H, CH3, 3.53 (d, J, 7.6 Hz, 2H, BnCH2, 5.38 (d, J, 16.1 Hz, 1H, 5.52 (t, J, 7.6 Hz, 1H, CHCH2, 5.90 (d, J, 16.1 Hz, 1H, 6.39 (s, 1H, OH, 10.14 (s, 1H, CHO, 12.70 (s, 1H, OH, 13C NMR (100 MHz CDCl3) δ 8.99, 10.4, 12.7, 14.6, 16.4, 22.3, 31.2, 40.9, 41.6, 48.5, 53.6, 113.1, 113.6, 113.7, 127.4, 133.1, 134.0, 135.6, 137.7, 156.0, 162.1, 193.1, 212.6; IR (film) 3268, 2960, 2925, 2871, 1708, 1614, 1454, 1423, 1375, 1328, 1282, 1249, 1172, 1110, 1012, 970, 906
- + 405.1754, found 405.1817.

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