The goal of this project is to transform an acyclic molecule (I ) into a tetracyclic target (L) using a tandem Diels-Alder/Pauson-Khand reaction, providing a new strategy to synthesize the steroid carbon skeleton.  We hypothesize that a cobalt-complexed alkyne will provide enough electron donation to activate a tandem Diels-Alder/Pauson-Khand reaction.  Our synthetic route to I  utilizes iodination via hydrozirconation, the Sonogashira reaction, and the Suzuki reaction.  The synthesis also employs MIDA boronate chemistry in the Sonogashira and Suzuki steps. 

Development of a tandem Diels-Alder/Pauson-Khand strategy for the synthesis of tetracycles

244th National Meeting (2012)

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