Multi-step reaction with 15 steps
1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane
2.1: chloro-trimethyl-silane; lithium diisopropyl amide / tetrahydrofuran
2.2: 12 h / Reflux
4.1: tetrabutyl ammonium fluoride
5.1: pyridine
6.1: potassium tert-butylate
7.1: lithium aluminium tetrahydride / diethyl ether / -20 °C
8.1: sodium hydrogencarbonate; Dess-Martin periodane
9.1: tetrahydrofuran / -78 °C
10.1: dmap / dichloromethane
11.1: diisobutylaluminium hydride / -78 °C
12.1: sodium hydrogencarbonate; Dess-Martin periodane
13.1: potassium fluoride / isopropyl alcohol / 24 h / 22 °C
14.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.17 h / 0 °C
15.1: 2,6-di-tert-butyl-4-methyl-phenol / benzene / 4 h / Inert atmosphere; Reflux
With
pyridine; dmap; potassium fluoride; lithium aluminium tetrahydride; chloro-trimethyl-silane; 2,6-di-tert-butyl-4-methyl-phenol; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; methanesulfonyl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane; isopropyl alcohol; benzene;
2.1: Claisen rearrangement / 2.2: Claisen rearrangement / 8.1: Dess-Martin oxidation / 9.1: Aldol condensation / 12.1: Dess-Martin oxidation / 13.1: Henry reaction / 15.1: Intramolecular Diels-Alder reaction;
DOI:10.1016/j.tetlet.2010.11.012