Multi-step reaction with 22 steps
1.1: aq. NaOH / methanol / 3.5 h / 100 °C
2.1: CSA / methanol / 0.5 h / 20 °C
3.1: NaH / tetrahydrofuran; dimethylformamide / 3.5 h / 20 °C
4.1: 1.14 g / CSA / acetone; H2O / 0.5 h / 70 °C
5.1: O3 / methanol; CH2Cl2 / -78 °C
5.2: Me2S / methanol; CH2Cl2 / 0.5 h / -78 °C
6.1: 4.30 g / CSA / benzene / 0.08 h / 90 °C
7.1: NaBH3(OAc)3; AcOH / acetonitrile / 4 h / 0 - 20 °C
8.1: Et3N / CH2Cl2 / 2 h / 20 °C
9.1: 26.6 g / TBAF / tetrahydrofuran / 2 h / 20 °C
10.1: 84 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
11.1: TMEDA; KHMDS / tetrahydrofuran; toluene / 0.5 h / 78 °C
11.2: 64 percent / tetrahydrofuran; toluene / -78 - 20 °C
12.1: SmI2; HMPA / tetrahydrofuran; methanol / -78 °C
13.1: 16.6 g / 2,6-lutidine / CH2Cl2 / 2.5 h / 20 °C
14.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -7 °C
14.2: tetrahydrofuran; hexane / 0.01 h / -78 °C
15.1: 12.6 mg / NaNO2; HCl / diethyl ether; H2O / 3 h / 0 °C
16.1: 79 percent / AcOH; Zn dust; NH4Cl / 50 °C
17.1: Ac2O / CH2Cl2 / 0 - 20 °C
18.1: LAH / tetrahydrofuran / 50 °C
19.1: 11.5 mg / Na2CO3 / CH2Cl2; H2O / 1 h / 20 °C
20.1: 88 percent / aq. HF / acetonitrile / 5 h / 0 °C
21.1: 1H-tetrazole / CH2Cl2 / 0 °C
21.2: 68 percent / TBHP / CH2Cl2; decane / 0.5 h / -78 °C
22.1: 63 percent / aq. HCl; H2 / Pd/C / methanol / 5 h / 20 °C / 760 Torr
With
2,6-dimethylpyridine; 1H-tetrazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; NaBH3(OAc)3; camphor-10-sulfonic acid; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; acetic anhydride; potassium hexamethylsilazane; sodium hydride; sodium carbonate; ammonium chloride; ozone; acetic acid; dimethyl sulfoxide; triethylamine; zinc; sodium nitrite;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
10.1: Swern oxidation;
DOI:10.1021/ol049074w