Multi-step reaction with 21 steps
1.1: 99 percent / NaI; DIPEA / CH2Cl2 / Heating
2.1: LiAlH4 / diethyl ether / 20 °C
3.1: 19.24 g / pyridine; DMAP / CH2Cl2 / 20 °C
4.1: O3 / methanol / -78 °C
4.2: 94 percent / NaBH4 / methanol / -78 - 0 °C
5.1: 96 percent / PPTS / CH2Cl2 / 20 °C
6.1: 99 percent / K2CO3 / methanol / 20 °C
7.1: 87 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
8.1: t-BuOK / tetrahydrofuran / 0.17 h / 0 °C
8.2: 100 percent / tetrahydrofuran / -78 - 20 °C
9.1: 100 percent / DIBAL-H / CH2Cl2 / -78 °C
10.1: 96 percent / 2,6-lutidine; MsCl; LiCl / dimethylformamide / 0 °C
11.1: 86 percent / HMPA; MeLi / diethyl ether / -65 °C
12.1: 100 percent / PPTs / ethanol / 20 °C
13.1: 92 percent / imidazole; I2 / benzene / 20 °C
14.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C
14.2: 84 percent / diethyl ether; pentane
15.1: 29 percent / TiCl3(Oi-Pr) / CH2Cl2 / 4 h / -78 °C
16.1: 9-BBN / tetrahydrofuran / 0 - 20 °C
16.2: 99 percent / NaOH; H2O2 / tetrahydrofuran / 20 °C
17.1: 93 percent / PPTS / CH2Cl2 / 20 °C
18.1: 100 percent / TBAF / tetrahydrofuran / 20 °C
19.1: 100 percent / triethylamine; DMAP / CH2Cl2 / 20 °C
20.1: 88 percent / PPTS / ethanol / 20 °C
21.1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; titanium(IV) trichloride isopropoxide; potassium tert-butylate; tetrabutyl ammonium fluoride; methyllithium; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; ozone; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; lithium chloride;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; pentane; benzene;
7.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol060437x