Multi-step reaction with 9 steps
1.1: 95 percent / ATPS / 12 h / 20 °C
2.1: 85 percent / LAH / tetrahydrofuran / 3 h / 0 °C
3.1: 100 percent / IBX / dimethylsulfoxide / 2 h / 20 °C
4.1: 81 percent / toluene / 10 h / 50 °C
5.1: 80 percent / DIBALH / tetrahydrofuran / 1 h / -78 °C
6.1: 95 percent / IBX / dimethylsulfoxide / 2 h / 20 °C
7.1: n-BuLi; (-)-sparteine / hexane / 3.17 h / -78 °C
7.2: Ti(O-i-Pr)4 / hexane; pentane / 0.5 h / -78 °C
7.3: 85 percent / hexane; pentane / 2 h / -78 °C
8.1: 70 percent / t-BuLi / diethyl ether / 0.75 h / -78 °C
9.1: 40 percent / DIAD; PPh3 / toluene / 0.17 h / -78 °C
With
lithium aluminium tetrahydride; n-butyllithium; adenosine-5'-O-(3-thiotriphosphate); di-isopropyl azodicarboxylate; tert.-butyl lithium; diisobutylaluminium hydride; triphenylphosphine; (-)-sparteine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; diethyl ether; hexane; dimethyl sulfoxide; toluene;
7.3: Hoppe crotylation;
DOI:10.1055/s-2005-864804