Multi-step reaction with 19 steps
1.1: 99 percent / SOCl2 / 6 h / 60 °C
2.1: 60 percent / PtO2; trifluoroacetic acid; H2 / 5 h / 25 °C / 2844.31 Torr
3.1: 99 percent / FeSO4*7H2O; aq. H2O2; TFA / air / 2 h / 0 °C
4.1: (R)-α,α-diphenyl-2-pyrrolidinemethanol; B(OMe)3; BH3*SMe2 / tetrahydrofuran / 0.5 h / 0 °C
5.1: Et3N / CH2Cl2 / 3 h / 25 °C
6.1: m-chloroperoxybenzoic acid / CH2Cl2 / 12 h / 25 °C
7.1: CH2Cl2 / 14 h / 0 - 25 °C
8.1: aq. K2CO3 / CH2Cl2 / 6 h / 25 °C
9.1: Burgess reagent / tetrahydrofuran / 0.33 h / 25 °C
10.1: Katsuki catalyst; 4-phenylpyridine N-oxide; NaOCl / CH2Cl2; aq. phosphate buffer / 1 h / 25 °C / pH 11.5
11.1: N-bromosuccinimide; 2,2'-azabisisobutyronitrile / CCl4 / 0.5 h / 80 °C
12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h / 25 °C
13.1: 36 mg / LiClO4 / acetonitrile / 22 h / 60 °C
14.1: 94 percent / i-Pr2NEt / tetrahydrofuran / 3 h / 0 - 25 °C
15.1: aq. NaOH / methanol / 5.5 h / 0 - 25 °C
16.1: Et3N; 2,4,6-trichlorobenzoyl chloride / toluene / 4 h / 25 °C
16.2: 64 percent / 4-dimethylaminopyridine / toluene / 14 h / 25 °C
17.1: PdCl2(PPh3)2; n-Bu3SnH / CH2Cl2 / 1 h / 0 °C
18.1: 250 mg / 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF6 / dimethylformamide / 1 h / 25 - 40 °C / sonication
19.1: 100 percent / n-Bu3SnH; PdCl2(PPh3)2 / CH2Cl2 / 0.58 h / -45 - 0 °C
With
platinum(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; sodium hypochlorite; N-Bromosuccinimide; thionyl chloride; 1-hydroxy-7-aza-benzotriazole; 4-Phenylpyridine 1-oxide; Burgess Reagent; Trimethyl borate; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; Katsuki catalyst; 2,4,6-trichlorobenzoyl chloride; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; lithium perchlorate; potassium carbonate; (R)-α,α-diphenylprolinol; iron(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; HATU; trifluoroacetic acid;
air;
In
tetrahydrofuran; methanol; tetrachloromethane; phosphate buffer; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
16.2: Yamaguchi-type esterification;
DOI:10.1021/ja0529337