Multi-step reaction with 13 steps
1: benzyl alcohol, 4A molecular sieves, Montmorillonite K10 / CH2Cl2 / 1 h / -45 °C
2: TBAF / tetrahydrofuran / Ambient temperature
3: Ph3P / tetrahydrofuran / 0.17 h / -23 °C
4: tetrahydrofuran / 168 h / Ambient temperature
5: t-BuOK / tetrahydrofuran / 1 h / 0 °C
6: tetrahydrofuran / 1 h / -78 °C
7: TMSOTf / CH2Cl2 / 1 h / -78 °C
8: 70 percent / TiCl3(O-i-Pr) / CH2Cl2 / 1 h / -78 °C
9: lithium tri(t-butoxy)aluminum hydride / tetrahydrofuran / Ambient temperature
10: 2,6-lutidine / CH2Cl2 / 1 h / -23 °C
11: DIBAL / CH2Cl2; hexane / 1 h / -78 °C
12: diethylzinc / diethyl ether; hexane / 6 h / Ambient temperature
13: PDC, 4A molecular sieves / CH2Cl2 / 1.5 h / Ambient temperature
With
2,6-dimethylpyridine; dipyridinium dichromate; titanium(IV) trichloride isopropoxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Montmorillonite K10; potassium tert-butylate; tetrabutyl ammonium fluoride; diethylzinc; diisobutylaluminium hydride; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; benzyl alcohol;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja984250f