Multi-step reaction with 13 steps
1.1: 58 percent / tetrahydrofuran / 12 h / 20 °C
2.1: 90 percent / (benzylidene)Ru(PCy3)2Cl2 / CH2Cl2 / 24 h / Heating
3.1: 83 percent / m-chloroperbenzoic acid / CH2Cl2 / 12 h / 0 °C
4.1: azidotrimethylsilane / (S,S)-Jacobsen Cr(salen) catalyst / diethyl ether / 144 h
4.2: 1S-(+)-10-camphorsulfuric acid / methanol / 0.5 h
5.1: NaH / tetrahydrofuran / 0.5 h / 20 °C
5.2: 88 percent / tetramethylammonium iodide / tetrahydrofuran / 0.5 h / 20 °C
6.1: 98 percent / H2 / Pd/C / methanol / 12 h / 20 °C
7.1: 73 percent / NaBH3CN; molecular sieves 4 Angstroem / methanol; acetic acid / 1 h / 20 °C / pH 6 - 7
8.1: 81 percent / Et3N / CH2Cl2 / 12 h / 20 °C
9.1: 91 percent / H2 / Pd/C / methanol / 12 h / 20 °C
10.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 0.5 h / 20 °C
11.1: n-BuLi / benzene; hexane / 1 h / 20 °C
11.2: 94 percent / benzene; hexane / 5 h / 20 °C
12.1: TBAF / tetrahydrofuran / 12 h / 20 °C
13.1: 92.8 mg / tetrahydrofuran / 2 h
With
pyridine; n-butyllithium; trimethylsilylazide; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium cyanoborohydride; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid;
palladium on activated charcoal; Grubbs catalyst first generation; (S,S)-Jacobsen Cr(salen) catalyst;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetic acid; benzene;
10.1: Dess-Martin oxidation / 11.1: Wittig reaction;
DOI:10.1021/ol016799g