Multi-step reaction with 15 steps
1.1: AD-mix β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 0 °C
2.1: CSA / CH2Cl2 / 20 °C
3.1: H2 / Pd/C / ethyl acetate; methanol / 20 °C
4.1: CSA / CH2Cl2 / 20 °C
5.1: 92 percent / KOt-Bu; n-Bu4NI / tetrahydrofuran / 20 °C
6.1: 100 percent / DIBAL-H / CH2Cl2 / -78 - 0 °C
7.1: 92 percent / I2; PPh3; imidazole / tetrahydrofuran / 20 °C
8.1: 99 percent / NaH / dimethylformamide / 0 - 20 °C
9.1: 9-BBN / tetrahydrofuran / 20 °C
9.2: aq. Cs2CO3 / PdCl2(dppf)*CH2Cl2 / tetrahydrofuran; dimethylformamide / 50 °C
10.1: thexylborane / tetrahydrofuran / 0 °C
10.2: 78 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 20 °C
11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 20 °C
12.1: TMSCl; LiHMDS; Et3N / tetrahydrofuran / -78 °C
12.2: Pd(OAc)2 / acetonitrile / 20 °C
13.1: 85 percent / DDQ / CH2Cl2 / 20 °C / pH 7
14.1: PPTS / toluene / 50 °C
15.1: Et3SiH; BF3*OEt2 / CH2Cl2; acetonitrile / -15 °C
With
1H-imidazole; triethylsilane; 9-borabicyclo[3.3.1]nonane dimer; chloro-trimethyl-silane; N-methyl-2-indolinone; tetrapropylammonium perruthennate; methanesulfonamide; 4 A molecular sieve; thexylborane; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; iodine; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;
9.1: Suzuki-Miyaura coupling / 9.2: Suzuki-Miyaura coupling;
DOI:10.1016/j.tetlet.2004.04.083