Multi-step reaction with 12 steps
1.1: 89 percent / NaH; TBAI / tetrahydrofuran / 3 h / 45 °C
2.1: aq. HCl / methanol; tetrahydrofuran / 25 h / 20 °C
3.1: 241 mg / 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
4.1: 91 percent / CSA / tetrahydrofuran; methanol / 0.5 h / -5 °C
5.1: 41.5 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 2 h / -60 - -45 °C
6.1: t-BuOK / tetrahydrofuran / 0.5 h / 0 °C
6.2: 36.2 mg / tetrahydrofuran / 0.83 h / 0 - 20 °C
7.1: 30.0 mg / TBAF / tetrahydrofuran / 1 h / 20 °C
8.1: AgOTf; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / -50 °C
8.2: 60.2 mg / CH2Cl2 / 1 h / -50 - -30 °C
9.1: 54.1 mg / TBAF / tetrahydrofuran / 0.5 h / 20 °C
10.1: 92 percent / ((Mes)2N2C3H4)Ru(=CHPH)Cl2(PCy3) / CH2Cl2 / 2 h / 20 °C
11.1: 100 percent / imidazole / dimethylformamide / 12 h / 20 °C
12.1: m-CPBA / CH2Cl2 / 3 h / -15 °C
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; hydrogenchloride; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
5.1: Swern oxidation / 6.2: Wittig reaction;
DOI:10.1021/ol0364475