Multi-step reaction with 10 steps
1.1: dmap; triethylamine / dichloromethane / 0 - 23 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / 0 °C / Inert atmosphere
3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere
4.1: water; barium(II) oxide / diethyl ether / 0 - 20 °C / Inert atmosphere
4.2: 48 h / 0 °C / Inert atmosphere
5.1: trimethyltin(IV) hydroxide / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; acetonitrile / -5 - 0 °C / Inert atmosphere
7.1: dmap; 2-methyl-6-nitrobenzoic anhydride / dichloromethane / 12 h / 20 °C / Inert atmosphere
8.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / -40 °C / Inert atmosphere
9.1: tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate; [Ph2PO-][NBu4+] / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere
10.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / benzene / 0 - 70 °C / Inert atmosphere
With
dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate; tributylphosphine; cerium(III) chloride heptahydrate; [Ph2PO-][NBu4+]; 2-methyl-6-nitrobenzoic anhydride; water; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; trimethyltin(IV) hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; barium(II) oxide; 1,1'-azodicarbonyl-dipiperidine;
In
methanol; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; benzene;
4.1: Horner-Wadsworth-Emmons reaction / 4.2: Horner-Wadsworth-Emmons reaction / 8.1: Luche reduction / 9.1: Stille coupling / 10.1: Mitsunobu reaction;
DOI:10.1021/ol201464m