- Access to Phenolic Fungal Metabolites via the Acid-catalysed Claisen Rearrangement. The Total Synthesis of (+/-)-Mellein, Aurocitrin, and 5',6'-Dihydroaurocitrin
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Regioselective trifluoroacetic acid catalysed rearrangement of allyl 5-allyloxy-2-hydroxybenzoate (2b) with concomitant cyclisation of the initial product permits the simple preparation of 3,4-dihydro-5,8-dihydroxy-3-methylisocoumarin (5).Hydrogenolysis of the non-hydrogen bonded hydroxy group yields (+/-)-mellein (7) whereas elaboration of the lactone moiety of compound (5) provides access to aurocitrin (8b) and its side chain analogues.
- Harwood, Laurence M.
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p. 2577 - 2582
(2007/10/02)
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- Total Synthesis of Frustulosin and Aurocitrin
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The regioselective total syntheses of the novel fungal antibiotics frustulosin (1) and aurocitrin (2) were accomplished from 3,6-dihydroxy-2-iodobenzaldehyde (10) which was prepared by a regiodirected metalation of 2,5-dimethylbenzyl vinyl ether to establish the 1,2,3,4-tetrasubstitution pattern of these compounds.The unsaturated side chains of these hydroquinone antibiotics were attached by using the iodo aldehyde functionalities.The structures of these antibiotics are confirmed by synthesis.
- Ronald, Robert C.,Lansinger, Janet M.,Lillie, Thomas S.,Wheeler, Carl J.
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p. 2541 - 2549
(2007/10/02)
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