反应条件
Multi-step reaction with 13 steps 1: 1.) sodium hydride / 1.) DME, RT, 10 min; 2.) DME, RT, overnight2: 1.) TMEDA, n-BuLi 2.) ClTi(O-iPr)3 / 1.) ether, hexane, -78 deg C, 1 h 2.) ether, hexane, -78 deg C, 2 h then -10 deg C, 1.5 h3: LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C / Heating4: PPTS / CH2Cl2 / 0.08 h / Ambient temperature5: 1.) B2H6, 2-methyl-2-butene 3.) 3M NaOH, 30percent aq. H2O2 / 1.) THF, -10 deg C, 2 h 2.) THF, 0 deg C, 30 min; 3.) THF, RT, 30 min.6: 90 percent / triphenylphosphine, imidazole, I2 / tetrahydrofuran; acetonitrile / 0.5 h / -10 °C7: 1.) NaH / 1.) DMSO, RT, 30 min; 2.) DMSO, overnight8: MeOH / PPTS / 0.08 h / Heating9: 1.) DMSO, (COCl)2 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min; 2.) CH2Cl2, -78 to 0 deg C10: 35 percent / K2CO3, 18-crown-6 / toluene / 80 °C11: H2O / PPTS / tetrahydrofuran / 1.5 h / Heating12: PCC, sodium acetate / CH2Cl2 / 2.5 h13: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min.
参考文献
Marshall, James A.; DeHoff, Bradley S. Tetrahedron, 1987 , vol. 43, # 21 p. 4849 - 4860