A base mediated cyclization is presented here as a method for the formation 6-5-6 indole fused ring systems. This method allows for access to these systems with a choice in functionality in the cyclized product. A methyl ester allows for subsequent Peterson olefination leading to the exocyclic alkene, while use of a Weinreb amide provides a ketone in the new six-membered ring. The BOC protecting group can be removed or retained depending on the choice of solvent. Application to the total synthesis of (+/-)-coerulescine is also described here.

Development of a method for the synthesis of 6-5-6 fused indole ring systems

246th National Meeting (2013)

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