期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 22, 页码 6722-6733出版社
WILEY-BLACKWELL
DOI: 10.1002/chem.200800495
关键词
allylic alkylation; carbocyclic nucleosides; cyclopentenones; iridium; phosphoramidites
A broadly applicable synthesis of chiral 2- or 2,4-substituted cyclopent-2-enones has been developed by combining asymmetric iridium-catalyzed allylic alkylation reactions and ruthenium-catalyzed ring-closing metathesis. Enantiomeric excesses (ee values) in the range of 95-99 % ee have been achieved. This method offers a straightforward access to biologically active prostaglandins of the PGA type. As an example, an enantioselective synthesis of the prostaglandin-analogue 13,14-dihydro-15-deoxy-Delta(7)-prostaglan-din-A1-methyl ester (TEI-9826) has been carried out. Furthermore, the carbonucleoside 2'-methylcarbovir has been prepared from O-protected 4-hydroxymethyl-2-methyl-cyclopent-2-en- one by Pd-catalyzed allylic amination.
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