Synthesis and plant growth promoting activity of dinorcholanic lactones bearing the 5α-hydroxy-6-oxo moiety

The naturally occurring dinorcholanic lactone vespertilin and two other non-natural derivatives bearing the 5α-hydroxy-6-oxo moiety were synthesized starting from the readily available steroid sapogenin diosgenin. The obtained compounds showed plant growth promoting activity in the bean's second internode elongation assay.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Synthesis of vespertilin by Beckmann rearrangement of 23-hydroximinodiosgenin. ► One-pot conversion of 3β-acetoxy-Δ5-steroids into 3β-acetoxy-5α-hydroxy-6-oxo-steroids. ► Vespertilin, a naturally occurring dinorcholanic lactone, promotes plant growth. ► Dinorcholanic lactones bearing the 5α-hydroxy-6-oxo moiety promote plant growth.