Multi-step reaction with 12 steps
1.1: 82 percent / diethyl ether / 1 h / 0 °C
2.1: NaH / tetrahydrofuran / 0 - 20 °C
2.2: 51 percent / tetrahydrofuran / 2 h / 20 °C
3.1: 91 percent / conc. H2SO4 / nitromethane / 0.5 h / 0 °C
4.1: 80 percent / m-chloroperbenzoic acid / ethyl acetate / 0 - 20 °C
5.1: 1.92 g / LDA / tetrahydrofuran / -40 - 20 °C
6.1: 60 percent / pyridinium chlorochromate / CH2Cl2 / 0 - 20 °C
7.1: p-toluenesulfonic acid; trimethyl orthoformate
7.2: 92 percent / HCl / acetone
8.1: 51 percent / DIBAL-H / petroleum ether / 1 h / -60 - 20 °C
9.1: nBuLi / tetrahydrofuran / -20 °C
9.2: 88 percent / tetrahydrofuran / 1 h / 0 - 20 °C
10.1: 88 percent / DIBAL-H / petroleum ether / -80 - -20 °C
11.1: 98 percent / HCl / acetone; H2O
12.1: LDA / tetrahydrofuran / 0.17 h / -20 °C
12.2: 68 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C
With
hydrogenchloride; n-butyllithium; sulfuric acid; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diisopropyl amide; trimethyl orthoformate;
In
tetrahydrofuran; diethyl ether; nitromethane; dichloromethane; water; ethyl acetate; acetone; Petroleum ether;
1.1: Methylation / 2.1: Metallation / 2.2: Condensation / 3.1: Cyclization / 4.1: Epoxidation / 5.1: Isomerization / 6.1: Oxidation / 7.1: Etherification / 7.2: Cyclization / 8.1: Reduction / 9.1: deprotonation / 9.2: Condensation / 10.1: Reduction / 11.1: deprotection / 12.1: Metallation / 12.2: Oxidation;
DOI:10.1002/(SICI)1099-0690(200003)2000:5<829::AID-EJOC829>3.0.CO;2-Z