Multi-step reaction with 18 steps
1.1: NaH / dimethylformamide / 1.5 h / 0 °C
1.2: Bu4NI / dimethylformamide / 15 h / 20 °C
2.1: 3.95 g / p-TsOH*H2O / methanol / 3 h / 40 - 70 °C
3.1: 2,6-lutidine / CH2Cl2 / 1.5 h / 20 °C
4.1: 4.77 g / CSA / CH2Cl2; methanol / 2 h / 0 °C
5.1: 94 percent / Et3N; SO3*pyridine / CH2Cl2; dimethylsulfoxide / 2.5 h / 20 °C / Parikh-Doering oxidation
6.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 0.33 h / -78 °C
6.2: 95 percent / tetrahydrofuran; pentane / 1.5 h / -78 °C
7.1: 93 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
8.1: 98 percent / methanol; tetrahydrofuran / 11 h / 20 °C
9.1: 93 percent / HF*pyridine; pyridine / tetrahydrofuran / 15 h / 20 °C
10.1: 87 percent / pyridinium p-toluenesulfonate / toluene / 3.5 h / 100 °C
11.1: 92 percent / DIBALH / toluene / 2 h / -78 °C
12.1: BH3*THF / tetrahydrofuran / 3 h / 0 - 20 °C
12.2: 91 percent / aq. NaOH; H2O2 / tetrahydrofuran / 3.5 h / 20 °C
13.1: 5.13 g / 2,6-lutidine / CH2Cl2 / 1.5 h / 20 °C
14.1: DDQ; phosphate buffer / CH2Cl2 / 1 h / 0 °C / pH 7
15.1: tetra-n-propylammonium perruthenate; NMO; molecular sieves 4 Angstroem / CH2Cl2 / 6.08 h / 0 - 20 °C
16.1: 2.89 g / TBAF; acetic acid / tetrahydrofuran / 7.5 h / 20 °C
17.1: 83 percent / TMSOTf; Et3SiH / acetonitrile / 0.25 h / -10 °C
18.1: 3.14 g / 2,6-lutidine / CH2Cl2 / 2.5 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; triethylsilane; N,N,N,N,N,N-hexamethylphosphoric triamide; N-methyl-2-indolinone; phosphate buffer; tetrapropylammonium perruthennate; borane-THF; oxalyl dichloride; pyridine-SO3 complex; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; pentane;
7.1: Swern oxidation;
DOI:10.1016/j.tet.2007.02.039