Only 90 µg of muironolide A was isolated from the same marine sponge that produced phorboxazole A. This was only enough to elucidate the structure of muironolide A leaving total synthesis as the only option to explore the biological activity. Our retrosynthetic plan relies on a convergent strategy that delivers three proposed fragments. Thus far, our efforts have focused on the synthesis of the isoindolinone core of muironolide A. After an unsuccessful intramolecular approach, we pursued an intermolecular Diels-Alder reaction leading to the synthesis of the isoindolinone core. This approach relies on the synthesis of an electronically deactivated and sterically hindered diene, but represents potentially straightforward access to the desired isoindolinone core.

Efforts toward synthesis of isoindolinone core of muironolide A

249th National Meeting (2015)

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