While safe for everyone else, ingestion of Averrhoa carambola, more commonly known as star fruit, can be harmful to chronic kidney disease patients; symptoms such as vomiting, mental confusion, and seizures and even deaths have been reported. Caramboxin has been identified as the active compound responsible for these effects and its molecular structure has been determined to contain an amino acid moiety, resembling a substituted phenylalanine. Our interest in caramboxin lies on its orsellinic acid-like aromatic ring, a feature present in several medically relevant natural products. Such compounds and their analogues are currently being investigated for the treatment of malaria, menopause symptoms, and various forms of cancer. We envision that caramboxin, as an amino acid, has the potential to be incorporated in peptide-based libraries for the development of novel drugs. With this in mind, synthetic access to large quantities of this rare active amino acid for biological studies is highly desirable. Given that the chirality of caramboxin has not been determined, the present project aims at its first total synthesis for structural confirmation. Furthermore, our synthetic route, which begins with aspartic acid, may provide a glimpse at how this molecule is produced in nature by Averrhoa carambola.

Developing a synthetic route to caramboxin, a rare bioactive non-peptidic amino acid

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