Synthesis of isoquinuclidinones via a tandem amination/imination sequence: application to the synthesis of (-)-mearsine

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The facile synthesis of a range of novel isoquinuclidinones from 6-acyl-cyclohex-2-enones is described, employing aqueous ammonia in a one-pot procedure involving initial conjugate addition of ammonia followed by cyclisation via intramolecular imine formation. The scope and limitations of the methodology are described as is an efficient synthesis of the Elaeocarpus alkaloid (-)-mearsine. (C) 2010 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)2024-2027
Number of pages4
JournalTetrahedron Letters
Issue number17
Publication statusPublished - 27 Apr 2011

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