By Shinsuke Inuki
The writer has constructed novel methodologies for hugely effective building of functionalized heterocycles by means of palladium-catalyzed domino/cascade cyclization of allenes and comparable compounds containing acceptable nucleophilic group(s). in keeping with those methodologies, enantioselective overall syntheses of bioactive common items, pachastrissamine (26% total yield in seven steps), lysergic acid (4.0% total yield in fifteen steps), lysergol (3.6% total yield in fifteen steps) and isolysergol (8.2% total yield in 11 steps) were accomplished. those are extra facile artificial course than these formerly suggested. those findings could give a contribution to the improvement of effective man made equipment for biologically energetic compounds containing a posh structure.
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Extra info for Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds
3 mmol) in CH2Cl2 (12 mL) at 0°C. 1, Entry 4). 1, Entry 8). 2671. 2670. 0 h at room temperature, followed by quenching with H2O. The whole was extracted with EtOAc. 1 mg, 69% yield). 2903. 2907. 2903. 0 h at room temperature, followed by quenching with saturated NH4Cl. The whole was extracted with EtOAc. The extract was washed with H2O and brine, dried over Na2SO4, and concentrated under pressure to give an oily residue, which was purified by column chromatography over silica gel with n-hexane–EtOAc (10:1) to give the corresponding tosylate as a colorless oil.
1 mL) at -30 °C under argon. 5 h at this temperature, the mixture was quenched with saturated NH4Cl. The whole was extracted with Et2O and the extract was washed with H2O and brine, and was dried over Na2SO4. 1805. 3, Entry 3). 44 mmol) at -78 °C under argon. The mixture was allowed to warm to 0 °C, and was stirred for 10 min at this temperature. 44 mmol) at -78 °C, and the mixture was allowed to warm to room temperature. The mixture was stirred for 30 min at this temperature. 1 mL) at -78 °C. After stirring for 30 min at this temperature, the mixture was quenched with saturated NH4Cl and 28% NH4OH.
The mixture was quenched by addition of 10 N NaOH at 0°C, and the whole was extracted with CHCl3. The extract was dried over Na2SO4. 2. Anal. 68. 57. 24 mmol) at 0°C. After stirring for 20 min at this temperature, the mixture was allowed to warm to room temperature. 0 h at this temperature and quenched with 2 N Rochelle salt. 0 h, the whole was extracted with EtOAc. The extract was washed with brine, and dried over Na2SO4. 3372. 8 mL) was stirred at 50°C under H2. 4 mL) was added to stirred mixture.