PIGMENTS OF FUNGI .41. SYNTHESIS OF (S)-(+)-DERMOLACTONE AND (+/-)-DERMOLACTONE - STEREOCHEMISTRY OF DERMOLACTONE FROM THE AUSTRALIAN FUNGUS DERMOCYBE-SANGUINEA (WULF EX FR) WUNSCHE SENSU CLELAND

被引:16
作者
COTTERILL, AS [1 ]
GILL, M [1 ]
MILANOVIC, NM [1 ]
机构
[1] UNIV MELBOURNE,SCH CHEM,PARKVILLE,VIC 3052,AUSTRALIA
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 10期
关键词
D O I
10.1039/p19950001215
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(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 H-1 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). .
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页码:1215 / 1223
页数:9
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