An Ireland-Claisen Rearrangement/Lactonisation Cascade as a Key Step in Studies Towards the Synthesis of (-)-Euonyminol:

Damian M Grainger,Matthew J Webber,Alexander Alanine,Stacy Lloyd,Lyn Powell,Sarah A Warren,Alan C Spivey,Andrew J P White,Christopher S Frampton,Jeffrey P Stonehouse,Matthew Weston

Synlett（2011）

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摘要

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 alpha-bromination of the resulting gamma-lactone.

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关键词

Ireland-Claisen,Celastraceae,bromination,euonyminol,sesquiterpene

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