Facile synthesis of novel D-ring modified steroidal dienamides via rearrangement of 2H-pyrans

A simple and practical method for synthesis of the D-ring modified steroidal dienamides (4a–k) from the steroidal α,α-dicyanoalkene 3 and aldehydes via vinylogous aldol reaction was first reported. By using NaOAc as a base, the desired products were obtained in moderate to good yields in ethanol under mild conditions. All the synthesized steroidal dienamides are new and are currently being evaluated for their biological activities.

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► Steroidal dienamides were first synthesized in moderate to good yields under mild conditions.
► Aldehydes reacted with steroidal α,α-dicyanoalkene to give the Steroidal dienamides.
► All the products were obtained via rearrangement of 2H-pyrans catalyzed by NaOAc.