反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
A 140 mg sample of 82 (0.23 mmol) was dissolved in CH2Cl2 (4 mL) and treated with DMBA (35.4 mg, 0.26 mmol) and Pd(PPh3)4 (32 mg, 0.028 mmol). The solution was stirred at 0° C. for 15 mins, warmed to room temperature for 2 hours, then diluted with CH2Cl2 and washed with water (2×) and brine. The solvent was concentrated in vacuo and the residue purified by flash chromatography on silica gel using MeOH/CH2Cl2 (1/99 to 3/97) to give the title compound (93.2 mg, 71% yield). 1H-NMR (500 MHz, CD3OD) δ 1.16 (d, 0.25H), 1.28-1.49 (m, 2.75H), 1.63-2.33 (m, 4H), 2.48 (dd, 0.4H), 3.39-3.59 (m, 0.2H), 3.60-3.73 (m, 0.8H), 3.73-3.96 (m, 1H), 4.24-4.48 (m, 2H), 4.57-4.92 (m, 7H), 5.44 (s, 0.4H), 5.50 (d, 0.4H), 5.64 (d, 0.8H), 5.75 (d, 0.5H), 7.16-7.43 (m, 5H), 7.78-7.89 (m, 1.6H), 8.40-8.63 (m, 0.4H). Analytical HPLC (cyano column) (mixture of 2 diastereomers) 11.57, 11.82 min. LC-MS (ES+) m/e=564.1 (M+H).
WORKUP
后处理
- temperaturewarmed to room temperature for 2 hours
- washwashed with water (2×) and brine
- concentrationThe solvent was concentrated in vacuo
- customthe residue purified by flash chromatography on silica gel