synthesis of pyran and pyranone natural products吡喃并吡喃酮的合成天然产物.pdfVIP

Molecules 2004, 9, 498–512 molecules ISSN 1420-3049 Synthesis of Pyran and Pyranone Natural Products† Christopher D. Donner, Melvyn Gill* and Leonie M. Tewierik School of Chemistry, The University of Melbourne, Parkville, Victoria 3010, Australia. Tel. (+61)-3- 8344-6485, Fax (+61)-9347-5180. * Author to whom correspondence should be addressed; e-mail: melvyn@.au Received: 25 March 2004 / Accepted: 5 April 2004 / Published: 31 May 2004 Abstract: An overview of the synthesis of the fungal metabolites (+)-dermolactone, (–)- semixanthomegnin, (+)- and (–)-mellein, (–)-ochratoxin α, (–)-(1R,3S)-thysanone, the enantiopure ventiloquinones L, E and G, and 8-desmethyleleutherin from a common chiral intermediate, is presented. Further methodology leading potentially toward extended quinones such as (3S,3S)-xylindein is also outlined. Keywords: Stereospecific synthesis; fungal metabolites; quinones; isochromanones. Introduction Biologically active aromatic systems with appended pyran or pyranone (δ-lactone) rings are widespread in nature, being found in a wide variety of organisms, including fungi. Our interest in these molecules was ignited by our need to synthesise just one member of the group in order to establish the absolute stereochemical configuration of that natural product, but has subsequently broadened in scope to become the first versatile total synthesis of a number of natural products in enantiomerically pure form. † Part 72 in the series, Pigments of Fungi. For Part 71 see Beattie, K.; Elsworth, C.; Gill, M.; M