Multi-step reaction with 12 steps
1.1: aq. LiBF4 / acetonitrile / 5 h / 0 - 20 °C
2.1: 17.87 g / LiCl; i-Pr2EtN / 1 h / 0 °C
3.1: 81 percent / Me2AlCl / CH2Cl2 / 1.5 h / -78 - -30 °C
4.1: 92 percent / K2OsO4; NMO / acetone; 2-methyl-propan-2-ol / 60 h / pH 7.0
5.1: 90 percent / p-toluenesulfonic acid hydrate / acetone / 1.5 h
6.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C
6.2: 94 percent / tetrahydrofuran; hexane / 0.5 h / 0 °C
7.1: 94 percent / DIBAL-H / toluene / 0.17 h / -90 °C
8.1: 92 percent / LiCl; i-Pr2EtN / acetonitrile / 24 h / 50 °C
9.1: 92 percent / DIBAL-H / toluene / -78 - -30 °C
10.1: TBAF; AcOH / tetrahydrofuran / 24 h
11.1: 91 percent / 2,6-lutidine / CH2Cl2 / 0.17 h / -78 °C
12.1: 98 percent / NaH / dimethylformamide; tetrahydrofuran
With
2,6-dimethylpyridine; potassium osmate(VI); lithium tetrafluoroborate; n-butyllithium; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; dimethylaluminum chloride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; lithium chloride;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;
2.1: Horner-Wadsworth-Emmons olefination / 3.1: Diels-Alder cycloaddition / 8.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja0684996