Multi-step reaction with 10 steps
1.1: piperidine / 5,5-dimethyl-1,3-cyclohexadiene / 0.5 h / 160 °C / Inert atmosphere
1.2: 3.5 h / 155 °C / Inert atmosphere
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere
3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 1 h / -78 - 0 °C / Inert atmosphere
4.2: 17 h / -78 - -20 °C / Inert atmosphere
5.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 - 20 °C
6.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere
6.2: 5 h / 0 - 20 °C / Inert atmosphere
7.1: sodium periodate / methanol / 0.5 h / 20 °C / pH 7 / aq. buffer; Inert atmosphere
8.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 1 h / -78 - 0 °C / Inert atmosphere
8.2: 46 h / -78 - -20 °C / Inert atmosphere
9.1: methanesulfonyl chloride; triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
10.1: (triphenylphosphine)copper(I) hydride hexamer; phenylsilane / toluene / 0.5 h / 0 - 20 °C / Inert atmosphere
With
piperidine; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; (triphenylphosphine)copper(I) hydride hexamer; phenylsilane; dicyclohexylboron chloride; sodium hydrogencarbonate; Dess-Martin periodane; methanesulfonyl chloride; triethylamine;
In
tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; diethyl ether; dichloromethane; toluene;
1.1: Knoevenagel reaction / 1.2: Knoevenagel reaction / 3.1: Dess-Martin oxidation / 4.1: Aldol condensation / 4.2: Aldol condensation / 8.1: Aldol condensation / 8.2: Aldol condensation;
DOI:10.1039/c2ob25100k