Multi-step reaction with 19 steps
1.1: O3 / CH2Cl2 / 0.25 h / -78 °C
1.2: 88 percent / PPh3 / CH2Cl2 / 4.5 h / -78 - 20 °C
2.1: Bu2BOTf; Et3N / CH2Cl2 / 60 h / -80 °C
2.2: 94 percent / phosphate buffer; aq. H2O2 / CH2Cl2; methanol / 6 h / 20 °C / pH 7.2
3.1: 99 percent / imidazole / dimethylformamide / 48 h / 40 °C
4.1: 96 percent / n-BuLi / hexane; tetrahydrofuran / 1.33 h / -78 - -15 °C
5.1: 99 percent / Et3SiH / Pd/C / acetone / 0.5 h / 20 °C
6.1: 49 percent / AgClO4 / Zr(Cp)2(H)(Cl) / CH2Cl2; toluene / 3 h / 0 - 20 °C
7.1: 97 percent / imidazole / dimethylformamide / 20 h
8.1: DDQ / CH2Cl2; H2O / 3.5 h / 0 °C
9.1: 2.14 g / Bu3P; pyridine / 3.5 h / 20 °C
10.1: 91 percent / aq. H2O2; PhSeSePh / diethyl ether / 29 h / -10 - 20 °C
11.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C
11.2: 86 percent / BF3*OEt2 / hexane; tetrahydrofuran / 1.5 h / -78 °C
12.1: 88 percent / lithium 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 1 h / -78 °C
13.1: 98 percent / DCC; DMAP / CH2Cl2 / 3 h / -5 - 0 °C
14.1: 70 percent / (+/-)-camphorsulfonic acid / CH2Cl2; methanol / 6 h / -20 - -10 °C
15.1: tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide / CH2Cl2 / 0.25 h
15.2: 85 percent / 2-methyl-2-butene; NaH2PO4; NaClO2 / 2-methyl-propan-2-ol; H2O / 1 h
16.1: piperidine / dimethylformamide / 0.08 h
17.1: 76 percent / CH2Cl2 / 3 h / 0 - 20 °C
18.1: 71 percent / EDCI; DMAP / CH2Cl2 / 20 °C
19.1: 68 percent / LHMDS / tetrahydrofuran / 0.08 h / -78 - -15 °C
With
piperidine; pyridine; 1H-imidazole; triethylsilane; dmap; n-butyllithium; tetrapropylammonium perruthennate; tributylphosphine; di-n-butylboryl trifluoromethanesulfonate; diphenyl diselenide; camphor-10-sulfonic acid; dihydrogen peroxide; silver perchlorate; lithium 4,4′-di-tert-butylbiphenylide; ozone; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
palladium on activated charcoal; Schwartz's reagent;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1002/anie.200500174