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Natural 4-Ylidenebutenolides and 4-Ylidenetetronic Acids

  • Chapter
Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Abstract

4-Ylidenebutenolides and 4-ylidenetetronic acids comprise a group of natural products many members of which have been discovered only in the past decade. The term “butenolide” describes the unsaturated γ-lactone system (1) and “tetronic acid” is the trivial name for 3-hydroxy- but-2-enolide (2). The corresponding 4-ylidene derivatives contain an additional exocyclic carbon-to-carbon double bond at C-4, and hence formulation (3) describes the 4-ylidenebutenolide, and (4) the 4-ylidene- tetronic acid, ring systems*. An excellent and comprehensive account of natural 4-ylidenebutenolides and 4-ylidenetetronic acids known up to 1962 has been given by Dean in his book (1). At this time the list numbered just thirteen metabolites, and included protoanemonin and matricaria lactone found in higher plants, patulin and dehydrocarolic acid isolated from fungi, and eight lichen pulvinic acid pigments. Today approximately seventy natural metabolites characterized structurally by the presence of one of the ring systems (3) or (4) are known. The early chemistry of butenolides has been well reviewed by Rao (2) and a useful account of tetronic acids is also available (3).

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  1. Department of Chemistry, The University, Nottingham, UK

    G. Pattenden

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Pattenden, G. (1978). Natural 4-Ylidenebutenolides and 4-Ylidenetetronic Acids. In: Herz, W., Grisebach, H., Kirby, G.W. (eds) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 35. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8505-6_3

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