Issue 10, 1995

Pigments of fungi. Part 41. Synthesis of (S)-(+)- and (±)-dermolactone; stereochemistry of dermolactone from the Australian fungus Dermocybe sanguinea(Wulf. ex Fr.) Wünsche sensu Cleland

Abstract

(S)-(+)-Dermolactone 3 has been synthesised in monochiral form beginning with ethyl (S)-lactate, the tetracyclic nucleus being assembled by way of a regiospecific cycloaddition between the known chloronaphthoquinone 15 and the novel, highly functionalised chiral butadiene derivative 5. Isochiral dermolactone 3+4 is prepared in the same way from (±)-5. Dermolactone, as it occurs naturally, is shown by 1H NMR shift experiments on the corresponding permethyl ethers 25 and 27, using [Eu(+)-(hfc)3], to consist of an anisochiral mixture of the (S)-(+)- and (R)-(–)-enantiomers 3 and 4, respectively, in which the former predominates in the ratio of 1.8:1 (28.6% ee).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1995, 1215-1223

Pigments of fungi. Part 41. Synthesis of (S)-(+)- and (±)-dermolactone; stereochemistry of dermolactone from the Australian fungus Dermocybe sanguinea(Wulf. ex Fr.) Wünsche sensu Cleland

A. S. Cotterill, M. Gill and N. M. Milanovic, J. Chem. Soc., Perkin Trans. 1, 1995, 1215 DOI: 10.1039/P19950001215

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