Multi-step reaction with 15 steps
1: 72 percent / K2CO3 / dimethylsulfoxide / 85 - 90 °C
2: 85 percent / K2CO3 / acetone / Heating
3: 80 percent / toluene / 180 - 190 °C
4: 1.) O3, 2.) NaBH3CN / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, i-PrOH
5: 72 percent / 135 °C
6: HN(SiMe3)2 / CH2Cl2; pentane / -20 °C
7: (PhSe)2 / tetrahydrofuran
8: 1.) O3, 2.) i-Pr2NH / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2
9: methanol / Heating
10: K2CO3, LiI / acetonitrile / 50 °C
11: 53 percent / PPh3, Et3N / Pd(OAc)2 / 90 °C
12: 67 percent / LiN(SiMe3)2 / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C
13: Zn, H2SO4 / methanol / Heating
14: NaH / methanol / Heating
15: 65 percent / DIBAL / toluene / -40 °C
With
sulfuric acid; diphenyl diselenide; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; ozone; triethylamine; diisopropylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium iodide; lithium hexamethyldisilazane; zinc;
palladium diacetate;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; dimethyl sulfoxide; acetone; toluene; acetonitrile; pentane;
DOI:10.1002/(SICI)1521-3773(19990201)38:3<395::AID-ANIE395>3.0.CO;2-5