Multi-step reaction with 11 steps
1.1: n-butyllithium; chloro-trimethyl-silane; (R)-2,2,2-trifluoro-N-(1-phenylethyl)ethan-1-amine / tetrahydrofuran; hexane / -78 °C / Inert atmosphere
1.2: 18 h / 20 °C
2.1: tributylphosphine; triethylamine / tetrahydrofuran; water / 21 h / 20 °C / Inert atmosphere
3.1: cerium(III) chloride heptahydrate / methanol / 0.25 h / 20 °C
3.2: 0.33 h / -78 °C
4.1: camphor-10-sulfonic acid / dichloromethane / 0.67 h / 20 °C / Molecular sieve
5.1: diisobutylaluminium hydride / dichloromethane / -78 - 20 °C / Inert atmosphere
6.1: triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere
7.1: lithium bromide / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
8.1: sodium hydride / tetrahydrofuran; mineral oil / 20 °C / Inert atmosphere; Reflux
8.2: 15 h / 20 °C
9.1: pyridinium p-toluenesulfonate / tetrahydrofuran; dichloromethane; ethylene glycol / 15 h / Reflux
10.1: sodium periodate / tetrahydrofuran; water
11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.67 h / 20 °C
With
sodium chlorite; sodium periodate; n-butyllithium; chloro-trimethyl-silane; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; tributylphosphine; cerium(III) chloride heptahydrate; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; triethylamine; (R)-2,2,2-trifluoro-N-(1-phenylethyl)ethan-1-amine; lithium bromide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; ethylene glycol; mineral oil; tert-butyl alcohol;
1.2: Saegusa oxidation / 2.1: Morita-Baylis-Hillman reaction / 3.1: Luche reduction / 3.2: Luche reduction;
DOI:10.1021/ol201498g