Multi-step reaction with 10 steps
1.1: 72 percent / BF3*OEt2 / acetic anhydride / 3 h / 0 °C
2.1: 85 percent / allyl methyl carbonate; DPPE; Bu3SnOMe / Pd(OAc)2 / acetonitrile / 5 h / 80 °C
3.1: 94 percent / DIBAL / tetrahydrofuran; hexane / 1.5 h / -78 °C
4.1: 76 percent / PCC; Celite / CH2Cl2 / 2 h
5.1: 85 percent / imidazole / dimethylformamide
6.1: 73 percent / I2; pyridine / CCl4
7.1: n-BuLi / diethyl ether; hexane
7.2: CuCN / diethyl ether; hexane
7.3: 62 percent / BF3*Et2O / diethyl ether; hexane / -78 °C
8.1: EtMgBr / tetrahydrofuran / 0.17 h / 0 °C
8.2: 66 percent / tetrahydrofuran / 2 h / 0 °C
9.1: Ni(acac)2 / tetrahydrofuran / 0.17 h / 0 °C
9.2: 93 percent / tetrahydrofuran
10.1: 73 percent / NaSEt / dimethylformamide / 12 h / 140 °C
With
pyridine; 1H-imidazole; bis(acetylacetonate)nickel(II); n-butyllithium; allyl methyl carbonate; Celite; boron trifluoride diethyl etherate; ethylmagnesium bromide; iodine; tributyltin methoxide; diisobutylaluminium hydride; pyridinium chlorochromate; 1,2-bis-(diphenylphosphino)ethane; sodium thioethylate;
palladium diacetate;
In
tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; dichloromethane; acetic anhydride; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo020457m