164801-78-9Relevant articles and documents
Pigments of fungi. Part 41. Synthesis of (S)-(+)- and (+/-)-dermolactone; stereochemistry of dermocactone from the Australian fungus Dermocybe sanguinea (Wulf. ex Fr.) Wuensche sensu Cleland
Cotterill, Ann S.,Gill, Melvyn,Milanovic, Nives M.
, p. 1215 - 1224 (2007/10/02)
(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 5.Isochiral dermolactone 3 + 4 is prepared in the same way from (+/-)-5.Dermolactone, as it occurs naturally, is shown by 1H NMR shift experimants on the corresponding permethyl ethers 25 and 27, using , 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 (28.6percent ee).
