90270-02-3合成路线 - 魔法化学

反应条件

1.1: 99 percent / SO3*pyridine; ethyldiisopropylamine / CH2Cl2; dimethylsulfoxide / 0 °C 2.1: sBuLi; (-)-(MeO)B(isopinocampheyl)2; BF3*OEt2 / tetrahydrofuran / 14 h / -78 °C 2.2: NaOH; H2O2 / H2O / -78 - 20 °C 3.1: sodium carbonate / methanol / 20 °C 4.1: 99 percent / sodium hydride; tetrabutylammonium iodide / dimethylformamide / 20 °C 5.1: N-methylmorpholine N-oxide; OsO4 / acetone; H2O / 20 °C 5.2: Pb(OAc)4 / benzene 6.1: tert-butyllithium / tetrahydrofuran / -96 - -78 °C 7.1: 99 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / -78 °C 8.1: 77 percent / tert-butyllithium; hexamethylphosphoramide / tetrahydrofuran / -78 - -40 °C 9.1: 84 percent / (bis(trifluoroacetoxy)iodo)benzene / tetrahydrofuran; H2O; methanol / 20 °C 10.1: 84 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 24 h / -5 °C 11.1: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 20 °C / pH 7 12.1: 99 percent / (COCl)2; dimethyl sulfoxide; triethylamine / CH2Cl2 13.1: 82 percent / CrCl2 / tetrahydrofuran / 0 - 20 °C 14.1: N-methylpyrrolidinone; [Pd{P(2-furyl)3}2Cl2]; hexamethyltin / 20 °C 14.2: [Pd{P(2-furyl)3}2Cl2]; N-methylpyrrolidinone / 20 °C 15.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C 16.1: 81 percent / 4-pyrrolidinopyridine / CH2Cl2 17.1: 89 percent / lithium hydroxide / H2O; tetrahydrofuran / 0 °C 18.1: 88 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 19.1: 66 percent / 2,6-lutidine / CH2Cl2 / -20 °C 20.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C 21.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C 22.1: 78 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C 23.1: 80 percent / dimedone / [Pd(PPh3)4] / tetrahydrofuran / 20 °C 24.1: PhI(OAc)2 / acetonitrile; H2O / 0 °C 25.1: 2,9-dimethyl-1,10-phenanthroline; pyridine / CH2Cl2 / 20 °C 26.1: 61 percent / pyridine*HF / tetrahydrofuran / 50 °C View Scheme

参考文献

Maddess, Matthew L.; Tackett, Miles N.; Watanabe, Hidenori; Brennan, Paul E.; Spilling, Christopher D.; Scott, James S.; Osborn, David P.; Ley, Steven V.
Angewandte Chemie - International Edition, 2007 , vol. 46, # 4 p. 591 - 597

90270-02-3

72522-40-87-羟基-4,6-二甲基壬烷-3-酮

参考文献

Masuda, Yui; Fujita, Ken; Mori, Kenji
Bioscience, Biotechnology and Biochemistry, 2003 , vol. 67, # 8 p. 1744 - 1750

90270-02-3

7184-60-3

反应条件

1.1: 98 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C 2.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 3.1: imidazole / dimethylformamide / 0 - 20 °C 4.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 5.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 6.2: tetrahydrofuran; hexane / 1 h / -30 °C 6.3: tetrahydrofuran; hexane / -20 °C 7.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 8.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 9.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 10.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 11.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 12.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 13.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 14.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 15.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 17.1: Et3N / benzene / 1 h / 20 °C 18.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 19.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 20.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 21.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 21.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: DMAP / pentane / 168 h / 20 °C 22.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 23.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 24.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 25.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 26.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 27.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 28.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 29.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 30.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 31.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 32.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 33.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 34.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

参考文献

Nagamitsu, Tohru; Takano, Daisuke; Marumoto, Kaori; Fukuda, Takeo; Furuya, Kentaro; Otoguro, Kazuhiko; Takeda, Kazuyoshi; Kuwajima, Isao; Harigaya, Yoshihiro; Omura, Satoshi
Journal of Organic Chemistry, 2007 , vol. 72, # 8 p. 2744 - 2756

90270-02-3

168134-57-4

参考文献

Ley, Steven V.; Tackett, Miles N.; Maddess, Matthew L.; Anderson, James C.; Brennan, Paul E.; Cappi, Michael W.; Heer, Jag P.; Helgen, Celine; Kori, Masakuni; Kouklovsky, Cyrille; Marsden, Stephen P.; Norman, Joanne; Osborn, David P.; Palomero, Maria A.; Pavey, John B. J.; Pinel, Catherine; Robinson, Lesley A.; Schnaubelt, Juergen; Scott, James S.; Spilling, Christopher D.; Watanabe, Hidenori; Wesson, Kieron E.; Willis, Michael C.
Chemistry - A European Journal, 2009 , vol. 15, # 12 p. 2874 - 2914