An Expedient Synthesis of the Antimitotic Natural Products Sarcodictyin and Eleutherobin, and Carbohydrate Analogues

Résumé fourni par la source

The eleutherobins and sarcodictyins are diterpenoids that belong to an elite family of microtubule-stabilizing natural products that includes the frontline cancer therapy Taxol. To date, members of this family of natural products have been overlooked as clinical candidates in large part, owing to a lack of material available from natural sources (rare marine invertebrates) or through chemical synthesis. Here, we report a concise synthesis of several members of the eleutherobin and sarcodictyin natural products using an approach that parallels Nature's strategy, with the assembly of a eunicellin intermediate followed by regio- and diastereoselective oxidations. Additionally, we report a collection of eleutherobin carbohydrate analogues that shed light on the relationship between carbohydrate structure and anticancer activity. These efforts should support and inspire the discovery of next-generation microtubule-stabilizing drugs.

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