A formal synthesis of (+)-muricatacin from L-tartaric acid.(GENERAL NOTES)(Report)

Muricatacin (1) is an acetogenin that displays cytotoxic activity towards certain tumor cell lines found in humans (Figure 1). This lipid-soluble class of anticancer drug was first isolated from the seeds of the Soursop tree (Annona muricata) and has received considerable attention in recent years. This paper describes a formal synthesis of (+)-muricatacin (1) using tartaric acid (2) as a chiral controller. The key step in this synthesis is the formation of butenolide 3 by way of intramolecular cyclization of 4a while under acidic conditions. The synthesis of 5S-(1S,2-dihydroxy-ethyl)-dihydro-furan-2-one (5), a formal precursor to 1 required six steps with an overall yield of ...

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