Multi-step reaction with 15 steps
1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux
2.1: asymmetric dihydroxylation-mix-α; hydroquinidein 1,4-phthalazinediyl diether / water; tert-butyl alcohol / 24 h / 0 °C / Inert atmosphere
3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere
3.2: 0.5 h / 0 - 20 °C / Inert atmosphere
4.1: magnesium; mercury dichloride / diethyl ether; toluene / 0 - 10 °C / Inert atmosphere
4.2: 1 h / 0 - 20 °C / Inert atmosphere
5.1: methylmagnesium bromide / tetrahydrofuran; diethyl ether / 6 h / 70 °C / Inert atmosphere
5.2: 5 h / 75 °C / Inert atmosphere
6.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.5 h / 0 - 20 °C / Inert atmosphere
7.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide / dichloromethane; water / 0.5 h / 0 °C / Inert atmosphere
8.1: ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethoxy))cyclopentadienyl-chlorotitanium / tetrahydrofuran; diethyl ether / 2 h / -78 - 0 °C / Inert atmosphere
8.2: 5 h / -78 °C / Inert atmosphere
9.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere
10.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 72 h / Inert atmosphere; Reflux
11.1: copper(l) iodide; tri-n-butyl-tin hydride; lithium chloride / tetrahydrofuran / 4 h / -40 - 0 °C / Inert atmosphere
12.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / pH 7.2 / aq. phosphate buffer; Inert atmosphere
13.1: tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 20 h / -30 °C / Inert atmosphere
14.1: 1H-imidazole / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere
15.1: toluene / Reflux; Inert atmosphere
With
1H-imidazole; sodium hypochlorite; copper(l) iodide; Hoveyda-Grubbs catalyst second generation; ammonium cerium (IV) nitrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; di-isopropyl azodicarboxylate; ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethoxy))cyclopentadienyl-chlorotitanium; asymmetric dihydroxylation-mix-α; methylmagnesium bromide; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; magnesium; methanesulfonyl chloride; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; mercury dichloride; potassium bromide; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; toluene; acetonitrile; tert-butyl alcohol;
1.1: Mitsunobu reaction / 2.1: Sharpless dihydroxylation;
DOI:10.1021/ol203064r