Multi-step reaction with 7 steps
1.1: methanol; lithium borohydride / diethyl ether / 0 - 20 °C
2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / 40 °C / Inert atmosphere
3.1: osmium(VIII) oxide; N,N,N,N,-tetramethylethylenediamine / dichloromethane / 14 h / -78 °C / Inert atmosphere
4.1: toluene-4-sulfonic acid / dichloromethane / 12 h / Inert atmosphere
5.1: tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide / dichloromethane / 3 h / Inert atmosphere; Molecular sieve
6.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 0.67 h / -78 °C / Inert atmosphere
6.2: -78 °C / Inert atmosphere
7.1: 2,6-dimethylpyridine; mercury(II) perchlorate tetrahydrate; water; calcium carbonate / tetrahydrofuran / 0.01 h / 0 °C
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; methanol; osmium(VIII) oxide; lithium borohydride; n-butyllithium; tetrapropylammonium perruthenate; mercury(II) perchlorate tetrahydrate; N,N,N,N,-tetramethylethylenediamine; water; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; calcium carbonate;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;
DOI:10.1021/ol3007259