Multi-step reaction with 16 steps
1.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 - -50 °C
1.2: -78 - 20 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 13 h / 0 - 20 °C
3.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; Cumene hydroperoxide / dichloromethane / 9 h / -40 - -25 °C / Molecular sieve
3.2: 1.5 h / -25 - 20 °C
4.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 13.83 h / 20 °C
5.1: potassium carbonate / methanol / 4 h / 20 °C
6.1: copper(l) iodide / tetrahydrofuran / 1.5 h / -40 °C
7.1: dmap; triethylamine / 2.5 h / 20 °C
8.1: osmium(VIII) oxide; AD-mix-β; 1,4-bis(9-O-dihydroquinidine)phthalazine / water; tert-butyl alcohol / 70 h / 0 - 20 °C
9.1: silica-supported sodium periodate / dichloromethane / 0.67 h / 0 - 20 °C
10.1: tetrahydrofuran / 13.83 h / -40 °C
11.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.33 h / -78 °C
11.2: -78 - 20 °C
12.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane / 44 h / -40 - -15 °C / Molecular sieve
12.2: 3 h / -15 - 20 °C
13.1: silver nitrate; triethylamine / tetrahydrofuran / 0.75 h / 0 °C
13.2: 15 h / 0 - 20 °C
14.1: camphor-10-sulfonic acid / methanol; dichloromethane / 2.5 h / 0 - 20 °C
15.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 3 h / 20 °C
16.1: potassium hexamethylsilazane / 1,2-dimethoxyethane / 0.5 h / -75 - -65 °C
16.2: 3 h / -75 - 0 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; copper(l) iodide; osmium(VIII) oxide; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; silica-supported sodium periodate; Cumene hydroperoxide; AD-mix-β; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; silver nitrate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; water; tert-butyl alcohol;
3.1: Sharpless epoxidation / 10.1: Wittig reaction / 12.1: Sharpless epoxidation / 16.1: Julia-Kocienski reaction / 16.2: Julia-Kocienski reaction;
DOI:10.1016/j.tet.2010.11.017