Convenient route to both enantiomers of a highly functionalized trans-disubstituted cyclopentene. Synthesis of the carbocyclic core of the nucleoside BCA.
Convenient route to both enantiomers of a highly functionalized trans-disubstituted cyclopentene. Synthesis of the carbocyclic core of the nucleoside BCA.
复制标题
获得高度官能化的反式二取代环戊烯的两种对映体的便捷途径。
DOI：
10.1021/jo0502504
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发表时间：
2005
期刊：
影响因子：
--
通讯作者：
Subrata K. Ghosh
中科院分区：
文献类型：
--
作者：
Shyamapada Banerjee;Sarita Ghosh;Saikat Sinha;Subrata K. Ghosh
[structures: see text] Synthesis of both enantiomers of a highly functionalized cyclopentenol derivative, versatile building block for a vast array of biologically active compounds, is described. The key steps involve stereocontrolled synthesis of a diene with two syn-disposed substituents from a (R)-(+)-glyceraldehyde derivative, ring-closing metathesis of this diene, and functional group manipulation of the resulting trans-disubstituted cyclopentene. One of the enantiomers of the cyclopentenol thus obtained has been converted to an amino cyclopentene, the carbocyclic core of the nucleoside (-)-BCA, a potent inhibitor of HIV reverse transcriptase.
