Issue 3, 1991
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Amide acetal Claisen rearrangement in the synthesis of mesembrane alkaloids

Sieglinde Bauermeister,   Izebrandt D. Gouws,   Heinrich F. Strauss  and  Elise M. M. Venter  

Abstract

The synthesis of primary and secondary allylic alcohols (differing in the degree of steric hindrance) and of amide acetals (achiral and chiral) is reported. These compounds were used as substrates in the amide acetal Claisen rearrangement, and the effect of Lewis acids on the stereoselectivity of the reaction was studied. The rearrangement products have been applied to the synthesis of the mesembrane alkaloids (–)-mesembranone, rac-O-methyljoubertiamine and joubertiamine.

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Article information

DOI
https://doi.org/10.1039/P19910000561
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1991, 561-565

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Amide acetal Claisen rearrangement in the synthesis of mesembrane alkaloids

S. Bauermeister, I. D. Gouws, H. F. Strauss and E. M. M. Venter, J. Chem. Soc., Perkin Trans. 1, 1991, 561 DOI: 10.1039/P19910000561

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