Multi-step reaction with 13 steps
1.1: KHMDS / toluene; tetrahydrofuran / 0.83 h / -78 - 20 °C
1.2: 76 percent / tetrahydrofuran; toluene / -78 - 20 °C
2.1: 96 percent / Na; MeOH / 2 h
3.1: 98 percent / H2; NaHCO3 / PtO2 / tetrahydrofuran / 20 h / 2585.81 Torr
4.1: 93 percent / Ph3P; DIAD / tetrahydrofuran / 0.08 h
5.1: 98 percent / MCPBA / CH2Cl2 / 0 - 20 °C
6.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C
6.2: 90 percent / tetrahydrofuran / -78 - 20 °C
7.1: Na; MeOH / 2 h
8.1: 97 percent / H2; NaHCO3 / PtO2 / tetrahydrofuran / 2585.81 Torr
9.1: 92 percent / Ph3P; DIAD / tetrahydrofuran
10.1: 91 percent / MCPBA / CH2Cl2 / 0 - 20 °C
11.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C
11.2: 90 percent / tetrahydrofuran / -78 - 20 °C
12.1: H2 / Pd/C / atmospheric pressure
13.1: tetrazole / acetonitrile
With
1H-tetrazole; methanol; di-isopropyl azodicarboxylate; hydrogen; sodium; potassium hexamethylsilazane; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane;
platinum(IV) oxide; palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; toluene; acetonitrile;
1.1: Wittig olefination / 1.2: Wittig olefination / 4.1: Mitsunobu reaction / 9.1: Mitsunobu reaction;
DOI:10.1021/ja0123958