Multi-step reaction with 15 steps
1.1: 313 mg / PPTS / dimethylformamide / 12.5 h / 20 °C
2.1: 318 mg / NaH; TBAI / tetrahydrofuran / 0.58 h / 20 °C
3.1: 286 mg / DBU; (PPh3)3RhCl / methanol; 1,2-dichloro-ethane / 0.25 h / 65 °C
4.1: 262 mg / pyridine / CH2Cl2 / 42 h / -18 - -5 °C
5.1: NaI; NiCl2(PPh3)2; n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C
5.2: 20 percent / t-BuCN / tetrahydrofuran; hexane / 2 h / 0 - 20 °C
6.1: 93 percent / TBAF / tetrahydrofuran / 20 °C
7.1: 89 percent / NaH; TBAI / tetrahydrofuran / 3 h / 45 °C
8.1: aq. HCl / methanol; tetrahydrofuran / 25 h / 20 °C
9.1: 241 mg / 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
10.1: 91 percent / CSA / tetrahydrofuran; methanol / 0.5 h / -5 °C
11.1: 41.5 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 2 h / -60 - -45 °C
12.1: t-BuOK / tetrahydrofuran / 0.5 h / 0 °C
12.2: 36.2 mg / tetrahydrofuran / 0.83 h / 0 - 20 °C
13.1: 30.0 mg / TBAF / tetrahydrofuran / 1 h / 20 °C
14.1: AgOTf; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / -50 °C
14.2: 60.2 mg / CH2Cl2 / 1 h / -50 - -30 °C
15.1: 54.1 mg / TBAF / tetrahydrofuran / 0.5 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; hydrogenchloride; Wilkinson's catalyst; bis(triphenylphosphine)nickel(II) chloride; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
11.1: Swern oxidation / 12.2: Wittig reaction;
DOI:10.1021/ol0364475