The synthesis of (�)-rhazinilam has been completed via an iterative C-H bond functionalization strategy. This synthesis utilizes direct metal catalyzed C-H arylation and a novel Pd-catalyzed C-H cyclization to install the key architecture directly from a simple pyrrole nucleus. A novel structural rearrangement converts rhazinilam to aspidospermidine, the reverse of the proposed biosynthesis of rhazinilam. We are currently investigating whether rhazinilam analogs can be transformed through a 'retrobiosynthesis' strategy to the vinca alkaloids.

Iterative metal-catalyzed C-H bond functionalization for complex natural product synthesis

240th National Meeting (2010)

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