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Synlett 2011(18): 2693-2696
DOI: 10.1055/s-0031-1289543
DOI: 10.1055/s-0031-1289543
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
An Ireland-Claisen Rearrangement/Lactonisation Cascade as a Key Step in Studies Towards the Synthesis of (-)-Euonyminol:
Further Information
Publication History
Received
30 August 2011
Publication Date:
19 October 2011 (online)


Abstract
Progress towards the asymmetric total synthesis of (-)-euonyminol is described with the focus on the installation of the oxygenation pattern on the lower rim of the molecule. An Ireland-Claisen rearrangement/lactonisation cascade has been developed and studies towards further elaboration have uncovered an intriguing tunable diastereoselective α-bromination of the resulting γ-lactone.
Key words
Ireland-Claisen - Celastraceae - bromination - euonyminol - sesquiterpene
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