Azaspirene is a recently discovered fungal metabolite with anti-angiogenic, and suspected anti-inflammatory properties. A milder type of chemotherapy shows promise: the utilization of angiogenesis inhibitors, particularly azaspirene.The presented work is innovative in three major ways; 1) it creates an entirely new efficient synthesis of the core structure of the inhibitor azaspirene; 2) it utilizes this route to produce an exploratory library; 3) it seeks to determine whether these novel drugs can effectively inhibit tumor angiogenesis, inflammation, and progression. Identification of chiral building blocks is the first step in the creation of a greatly simplified total synthesis that is economically more viable than other reported synthetic routes. The presented procedure allows us to initiate the synthesis with most of the oxygen atoms already contained with correct stereochemistry within the molecule which reduces the need for oxidation reactions to create the highly oxygenated molecule of the pseurotin analog library.

Diversity oriented total synthesis of analogs derived from azaspirene: Powerful inhibitor of angiogenesis and inflammation

243rd National Meeting (2012)

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