Multi-step reaction with 21 steps
1.1: 9-BBN / tetrahydrofuran / 2.5 h / 20 °C
1.2: 9.46 g / Pd(PPh3)4; aq. NaHCO3 / dimethylformamide; tetrahydrofuran / 14 h / 50 °C
2.1: BH3*SMe2 / tetrahydrofuran / 4 h / 0 °C
2.2: 2.98 g / aq. H2O2; NaOH / tetrahydrofuran / 2.5 h / 20 °C
3.1: 96 percent / 2,6-lutidine / CH2Cl2 / 1.5 h / 0 °C
4.1: 88 percent / DDQ; aq. phosphate buffer / CH2Cl2 / 1 h / 20 °C / pH 7
5.1: 92 percent / N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate; 4A molecular sieves / CH2Cl2 / 1 h / 20 °C
6.1: 1.62 g / Zn(OTf)2 / CH2Cl2 / 25 h / 20 °C
7.1: 1.75 g / camphorsulfonic acid / CH2Cl2 / 2.5 h / 20 °C
8.1: 78 percent / Ph3SnH; AIBN / toluene / 4 h / 110 °C
9.1: lithium 4,4'-di-tert-butylbiphenylide / tetrahydrofuran / 2 h / -78 °C
10.1: 0.972 g / pyridine / CH2Cl2 / 1.5 h / 20 °C
11.1: 81 percent / N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate; 4A molecular sieves / CH2Cl2 / 1 h / 20 °C
12.1: LHMDS; Et3N / tetrahydrofuran / 0.42 h / -78 °C
13.1: 587.4 mg / Pd(OAc)2 / acetonitrile / 15 h / 20 °C
14.1: 88 percent / NaBH4; CeCl3*7H2O / CH2Cl2; methanol / 0.5 h / 0 °C
15.1: 83 percent / NaHCO3; mCPBA / CH2Cl2 / 11.5 h / 20 °C
16.1: 81 percent / N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate; 4A molecular sieves / CH2Cl2 / 1 h / 20 °C
17.1: 100 percent / Na[PhSeB(OEt)3] / ethanol / 0 - 20 °C
18.1: camphorsulfonic acid / CH2Cl2 / 4 h / 20 °C
19.1: L-Selectride / tetrahydrofuran / 0.75 h / -78 °C
20.1: 78.8 mg / LiAlH4 / tetrahydrofuran / 0.67 h / 0 °C
21.1: 81 percent / Et3N; DMAP / CH2Cl2 / 20 °C
With
pyridine; 2,6-dimethylpyridine; dmap; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; cerium(III) chloride; tetrapropylammonium perruthennate; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; 4 A molecular sieve; camphor-10-sulfonic acid; triphenylstannane; L-Selectride; zinc trifluoromethanesulfonate; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; sodium phenylseleno(triethyl)borate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; acetonitrile;
1.2: Suzuki-Miyaura cross-coupling / 14.1: Luche reduction;
DOI:10.1021/ja042686r