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.

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► 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.