Steroids 35: Synthesis of 16,16-dimethyl-17β-hydroxysteroids

The reaction of 16-methylene-17-ketosteroids (Ia), (Ic) and (Ie) with methyl magnesium iodide yields 16-methylene-17α-methyl-17β-hydroxysteroids (IIa), (IIb) and (IId). These are subjected to the addition of hypobromous acid and the subsequent anionotropic rearrangement to convert them into 16α-meth...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Steroids 1988-03, Vol.51 (3), p.317-327
Hauptverfasser:	Schneider, Gyula, Wolfling, Janos, Mesko, Eszter, Dombi, Gyorgy
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds, terpenoids, prostaglandins, steroids Chemical Phenomena Chemistry Exact sciences and technology Hydroxysteroids - chemical synthesis Organic chemistry Preparations and properties Steroids
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	The reaction of 16-methylene-17-ketosteroids (Ia), (Ic) and (Ie) with methyl magnesium iodide yields 16-methylene-17α-methyl-17β-hydroxysteroids (IIa), (IIb) and (IId). These are subjected to the addition of hypobromous acid and the subsequent anionotropic rearrangement to convert them into 16α-methyl-16β-bromomethyl -17-ketosteroids (Va), (Vb) and (Vd). These were reduced with LiAlH 4 to obtain 16,16-dimethyl-17β-hydroxysteroids (VIa), (VIb) and (VId). Compounds (VIIa) and (VIIe) were selectively deacetylated yielding (VIIb) and (VIId); these were then oxidized and hydrolyzed to convert them into (VIf) and (VIg).
ISSN:	0039-128X 1878-5867
DOI:	10.1016/0039-128X(88)90021-9