Recent developments in natural product synthesis

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Abstract
During work on the total synthesis of the novel ionophore antibiotic tetronasin, new methodology for the preparation of acyltetronic acids and 6-ketonacrol ides and diol ides has been developed using t-butylacetothioacetate as a key building block. Further chemistry established a new route to 6-ketoamides which in turn were used as precursors for acyltetramic acid preparation including a total synthesis of the plasmodia1 pigment fuligorubin A. Tetronasin (ICI 14139603) is a structurally novel acyl tetronic acid ionophore antibiotic discovered in 1981 and is presently being developed as a ruminant growth promotion agent. Lle became interested in the synthesis of tetronasin owing to the unusual cyclohexyl group and the terminal acyltetronic acid which had not been previously observed in other ionophore antibiotics. Tetronasin presents an interesting synthetic challenge as it contains 12 chiral centres isolated in five separate regions of the molecule.

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