This communication describes two approaches toward the total synthesis of (+)-suaveolindole. The initial strategy uses a 6exo -Heck cyclization to generate a transient Sp3 Carbopalladate. This intermediate was successfully coupled with an indole 3stannane to assemble the majority of the carbon framework of the natural product. However, due to problems described herein, this interesting route was not viable. To reach our target, lessons learned from the first strategy directed us to develop a significant extension of the Ireland ester enolate rearrangement in which the tetra -substituted isopropylidene group and the a-disposed carboxymethyl function are introduced in a single event. This key reaction enables a remarkably concise inaugural synthesis of suaveolindole.