Rearrangement Reactions

Pollex, A.; Hiersemann, Martin

doi:10.1002/3527606858.ch5

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2009

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“…The Claisen rearrangement was an attractive alternative to form a quaternary carbon center, but there are scant examples of this reported in the literature and they mostly involve rigid cyclic molecules . Regardless of the variant used (Claisen−Ireland, Carroll, Johnson−Claisen, etc.…”

Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis of (+)-Euphococcinine and (−)-Adaline

et al. 2009

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We describe the syntheses of (+)-euphococcinine and (-)-adaline, two naturally occurring alkaloids containing a quaternary carbon bearing a nitrogen atom. Key features of the syntheses are a 3,3-sigmatropic rearrangement to give an all-carbon quaternary center, a ring-closing alkene metathesis to give an 8-membered ring, and the use of a single enantiomer of p-menthane-3-carboxaldehyde to make two natural alkaloids of opposite configuration.

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Section: Resultsmentioning

confidence: 99%