A TOTAL SYNTHESIS OF RACEMIC AND OPTICALLY-ACTIVE TERREIN (TRANS-4,5-DIHYDROXY-3-[(E)-1-PROPENYL]-2-CYCLOPENTEN-1-ONE)

被引:54
作者
KOLB, HC [1 ]
HOFFMANN, HMR [1 ]
机构
[1] UNIV HANOVER,DEPT ORGAN CHEM,W-3000 HANOVER,GERMANY
关键词
D O I
10.1016/S0957-4166(00)86329-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two routes to terrein (1), employing a novel ring contraction of 6-alkoxy-2,3-dihydro-6H-pyran-3-ones (5, 13) are described. Separation into enantiomers was carried out by classical resolution via diastereomeric camphanic acid ester intermediates (14, 15). A new method for cleavage of the 2-(trimethylsilyl)ethyl protecting group in the presence of acid and base sensitive functionality is reported. © 1990.
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页码:237 / 250
页数:14
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