Multi-step reaction with 15 steps
1.1: toluene-4-sulfonic acid / acetone / 4 h / 0 - 20 °C
2.1: 1H-imidazole; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C
2.2: 0.5 h / 20 °C
2.3: 0.17 h
3.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 2.5 h / 60 °C / Reflux
4.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tert-butyl alcohol / 20 °C / pH 7
4.2: 3407 / 4 h / 20 °C / pH 7
5.1: dichloromethane / 1 h / 20 °C
6.1: diisobutylaluminium hydride / toluene; hexane / -78 - 0 °C
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 0 - 20 °C
8.1: AD-mix-β; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium osmate(VI) dihydrate; methanesulfonamide / tert-butyl alcohol / pH 7
9.1: toluene-4-sulfonic acid / acetone / 4 h / 0 - 20 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C
11.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.33 h / -60 °C
11.2: -60 - 20 °C
12.1: potassium tert-butylate / tetrahydrofuran / -10 - 20 °C
12.2: -10 - 20 °C
13.1: hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); potassium carbonate; potassium osmate(VI) dihydrate; methanesulfonamide / tert-butyl alcohol / pH 7
14.1: pyridinium p-toluenesulfonate; Trimethyl orthoacetate / dichloromethane / 2 h / 20 °C
14.2: 5 h / 20 °C
14.3: 20 °C
15.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C
15.2: 1 h / -78 °C
With
1H-imidazole; Trimethyl orthoacetate; potassium osmate(VI) dihydrate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); methanesulfonamide; AD-mix-β; potassium tert-butylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III);
In
tetrahydrofuran; hexane; dichloromethane; acetone; toluene; mineral oil; tert-butyl alcohol; benzene;
3.1: |Barton-McCombie Deoxygenation / 8.1: |Sharpless Dihydroxylation / 11.1: |Swern Oxidation / 11.2: |Swern Oxidation / 13.1: |Sharpless Dihydroxylation;
DOI:10.1016/j.tet.2013.05.067