(2R,4R)-16-Heptadecene-1,2,4-triol synthesis

Yield:-

Steps:

Multi-step reaction with 10 steps
1.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 1.5 h / -78 - 20 °C
1.2: 3 h / -20 - 20 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h
3.1: potassium hydride; Trimethylenediamine / mineral oil / 10 h / 0 - 20 °C
4.1: dipyridinium dichromate / dichloromethane / 18 h / 20 °C
5.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
6.1: triethylamine; formic acid; [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5,6-η)-1,3,5-trimethylbenzene]-ruthenium / N,N-dimethyl-formamide / 1 h / 0 °C
7.1: diethyl methoxy borane / tetrahydrofuran; methanol / 0.25 h / -78 °C
7.2: 5 h / -78 °C
8.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 3.5 h / -78 - 20 °C
9.1: tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate / dichloromethane / 1 h / 20 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran; N,N-dimethyl-formamide / 15 h / 80 °C

References:

Cunha, Vitor L. S.;Liu, Xiaofan;Lowary, Todd L.;O'Doherty, George A. [Journal of Organic Chemistry,2019,vol. 84,# 23,p. 15718 - 15725]