I was thinking possible intramolecular michael reaction by adding EtO-K+ in EtOH, then adding 1-propanone and then getting rid of the resulting OH group on the 5 carbon ring and forming that double bond by adding NaOH and heat.
Or possible doing an organcuprate reaction with LiCu(CH2CH2CHO)2 and reducing the ketone in the 5 carbon ring with NaOH, H2O and heat.
Either of these seem like reasonable, efficient syntheses?