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

Article Excerpt
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 11%.

The [gamma]-butyrolactone (or furanone) ring system is present in a number of naturally occurring compounds, many of which are biologically active (Couladouros et al. 1999 and references cited therein). Chiral hydroxylactones have also proven to be effective as antifeedants (Hidefumi et al. 1984) and some have displayed cytotoxic properties against human tumor...

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