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

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JournalTetrahedron Letters
DatePublished - 27 Apr 2011
Issue number17
Volume52
Number of pages4
Pages (from-to)2024-2027
Original languageEnglish

Abstract

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.

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