Multi-step reaction with 13 steps
1.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetone / 24 h / Reflux
2.1: 2 h / 200 °C
3.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetone / 24 h / Reflux
4.1: (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II) / tetrahydrofuran / 3 h / Reflux
5.1: 2,6-dimethylpyridine; osmium(VIII) oxide; sodium periodate / 1,4-dioxane; water; tert-butyl alcohol / 0.5 h
6.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.08 h / 0 °C
7.1: phosphorus tribromide / tetrahydrofuran; dichloromethane / 4.5 h / 0 °C
8.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C
8.2: 0.5 h / -78 °C
9.1: methanol; lithium borohydride / tetrahydrofuran; diethyl ether / 5 h
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3 h / 20 °C
11.1: lithium chloride / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3 h / 20 °C
13.1: triethylamine; (+)-β-chlorodiisopinocampheylborane / diethyl ether / 1 h / -78 - 0 °C
13.2: 2 h / -78 °C
With
2,6-dimethylpyridine; methanol; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium borohydride; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); (+)-β-chlorodiisopinocampheylborane; sodium hexamethyldisilazane; phosphorus tribromide; tetra-(n-butyl)ammonium iodide; potassium carbonate; triethylamine; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol;
DOI:10.1021/ol303482k