Terpene molecules are widely represented in nature and many are relevant from a pharmaceutical standpoint. Unfortunately, natural abundance can be low and chemical synthesis remains an outstanding challenge. In order to tackle these limitations, we have devised a simple and scalable methodology to access terpenoid cores using readily available reagents. Using this approach, simple cyclic ketones were converted to decorated 5-7 or 6-7 fused bicyclic systems in only 3 steps. We wish to expand this methodology to the synthesis of pharmaceutically relevant tricyclic terpenes and their analogs. Presented is our progress to date toward dolestane and pseudo-guaianolide natural products.

Analog oriented synthesis of terpenoid cores: toward dolestane and pseudo-guaianolide architectures

255th National Meeting (2018)

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