Straightforward Synthesis of (R)‐(−)‐Kjellmanianone
- 16 February 2004
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 10 (4) , 1042-1045
- https://doi.org/10.1002/chem.200305486
Abstract
A direct route to enantiomerically pure (−)-kjellmanianone is reported. The synthesis involves a cerium-catalyzed α-hydroxylation and an enzyme-catalyzed procedure to resolve tertiary alcohols at key stages. The intermediate β-oxo ester was α-hydroxylated to give good yields of racemic kjellmanianone. The resolution of the racemic material was achieved by enzymatic saponification, followed by a chemical decarboxylation sequence to give enantiopure (−)-kjellmanianone with 99 % ee. Bromination then afforded the (−)-bromo derivative, whose X-ray structure provided evidence for the R configuration of (−)-kjellmanianone.Keywords
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