Multi-step reaction with 23 steps
1.1: 87 percent / DIBALH / tetrahydrofuran / -78 °C
2.1: 99 percent / (+/-)-CSA / 50 °C
3.1: Et3N; DMAP / dimethylformamide / 0 - 20 °C
4.1: LiAlH4 / diethyl ether / 0 - 20 °C
5.1: NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C
6.1: TBAF / tetrahydrofuran / 20 °C
7.1: Et3N / CH2Cl2 / 0 °C
8.1: NaI / acetone / Heating
9.1: BuLi / tetrahydrofuran / -78 - 20 °C
9.2: tetrahydrofuran / -78 - 20 °C
10.1: (+/-)-CSA / methanol; H2O / 60 °C
11.1: 72 percent / diethyl ether / -78 °C
12.1: aq. AcOH / 60 °C
13.1: 1,2-dichloro-ethane / 80 °C
14.1: 68 percent / Et3N; DMAP / dimethylformamide / 40 °C
15.1: 87 percent / PDC; 4 Angstroem molecular sieves / CH2Cl2 / 20 °C
16.1: 81 percent / NaBH4 / methanol / 0 °C
17.1: CBr4; Ph3P / CH2Cl2 / 20 °C
18.1: 55 percent / SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 20 °C
19.1: 78 percent / DIBALH / diethyl ether / -78 °C
20.1: Bu3P; pyridine / 20 °C
21.1: MCPBA / CH2Cl2
22.1: i-Pr2NEt / 1,2-dichloro-benzene / 160 °C
23.1: 95 percent / Na; NH3 / tetrahydrofuran / -78 °C
With
pyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; samarium diiodide; carbon tetrabromide; tributylphosphine; 4 A molecular sieve; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; ammonia; sodium; sodium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium iodide;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone;
13.1: Wittig reaction;