Multi-step reaction with 11 steps
1.1: copper(l) iodide / tetrahydrofuran / 1.5 h / -40 °C
2.1: dmap; triethylamine / 2.5 h / 20 °C
3.1: osmium(VIII) oxide; AD-mix-β; 1,4-bis(9-O-dihydroquinidine)phthalazine / water; tert-butyl alcohol / 70 h / 0 - 20 °C
4.1: silica-supported sodium periodate / dichloromethane / 0.67 h / 0 - 20 °C
5.1: tetrahydrofuran / 13.83 h / -40 °C
6.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.33 h / -78 °C
6.2: -78 - 20 °C
7.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane / 44 h / -40 - -15 °C / Molecular sieve
7.2: 3 h / -15 - 20 °C
8.1: silver nitrate; triethylamine / tetrahydrofuran / 0.75 h / 0 °C
8.2: 15 h / 0 - 20 °C
9.1: camphor-10-sulfonic acid / methanol; dichloromethane / 2.5 h / 0 - 20 °C
10.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 3 h / 20 °C
11.1: potassium hexamethylsilazane / 1,2-dimethoxyethane / 0.5 h / -75 - -65 °C
11.2: 3 h / -75 - 0 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; copper(l) iodide; osmium(VIII) oxide; diethyl (2S,3S)-tartrate; silica-supported sodium periodate; AD-mix-β; camphor-10-sulfonic acid; potassium hexamethylsilazane; diisobutylaluminium hydride; 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;
5.1: Wittig reaction / 7.1: Sharpless epoxidation / 11.1: Julia-Kocienski reaction / 11.2: Julia-Kocienski reaction;
DOI:10.1016/j.tet.2010.11.017