Multi-step reaction with 25 steps
1.1: NaOMe / methanol; CH2Cl2 / 3.5 h / 0 °C
2.1: 78 percent / pyridine / dimethylformamide / -40 °C
3.1: 90 percent / KOBu-t / tetrahydrofuran / 0.5 h / 0 °C
4.1: 77 percent / lithium naphthalenide / tetrahydrofuran / -78 - -10 °C
5.1: 89 percent / imidazole / dimethylformamide / 12 h / 20 °C
6.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C
6.2: 100 percent / tetrahydrofuran; pentane / -78 - 20 °C
7.1: 96 percent / dimethyl dioxirane / CH2Cl2; diethyl ether / 0.25 h / -78 °C
8.1: 100 percent / NaH / hexamethylphosphoric acid triamide / 0.83 h / 0 °C
9.1: 96 percent / iPr2NEt / CH2Cl2 / -78 °C
10.1: 92 percent / DCC; DMAP / CH2Cl2 / 0 - 20 °C
11.1: 91 percent / 10-camphorsulfonic acid / methanol / 0.08 h / 0 °C
12.1: NaH / 4 h / 20 °C
12.2: 0.5 h / 20 °C
13.1: 0.046 g / n-Bu3SnH; AIBN / benzene / 1.5 h / Heating
14.1: 100 percent / TiCl4; TMEDA; Zn dust / PbCl2 / CH2Cl2; tetrahydrofuran / 2 h
15.1: 0.038 g / Grubbs second generation catalyst / benzene / 36 h / Heating
16.1: dimethyl dioxirane / CH2Cl2; acetone / -78 - 0 °C
16.2: 95 percent / DIBAL / CH2Cl2; hexane / 2 h / -78 °C
17.1: 80 percent / PPTS; pyridine / chlorobenzene / 48 h / Heating
18.1: 76 percent / H2 / PtO2*H2O / hexane; ethyl acetate / 5.5 h / 760.05 Torr
19.1: 94 percent / HF*pyridine / tetrahydrofuran / 1 h / 0 °C
20.1: CH2Cl2 / 0.25 h / -78 °C
20.2: 2,6-lutidine / CH2Cl2 / 0.5 h / 20 °C
21.1: CuI / tetrahydrofuran / -78 - 0 °C
21.2: tetrahydrofuran / 2 h / -40 °C
22.1: 0.0016 g / 10-camphorsulfonic acid / methanol / 1 h / 0 °C
23.1: 2,4,6-trichlorobenzoyl chloride; NEt3 / tetrahydrofuran / 2 h / 40 °C
23.2: 69 percent / DMAP / toluene / 2 h / 40 °C
24.1: 100 percent / TiCl4; TMEDA; Zn / PbCl2 / CH2Cl2 / 65 °C
25.1: Schrock Mo catalyst / hexane / 60 °C
With
pyridine; 1H-imidazole; dmap; copper(l) iodide; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; 2,4,6-trichlorobenzoyl chloride; (1S)-10-camphorsulfonic acid; potassium tert-butylate; hydrogen; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium methylate; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydride; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; naphthalen-1-yl-lithium; dicyclohexyl-carbodiimide; zinc;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; platinum(IV) oxide; lead(II) chloride;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; chlorobenzene; acetone; pentane; benzene;
DOI:10.1021/ol0707970