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

TY - JOUR

T1 - Synthesis of isoquinuclidinones via a tandem amination/imination sequence: application to the synthesis of (-)-mearsine

AU - Cuthbertson, James D.

AU - Godfrey, Andrew A.

AU - Taylor, Richard J. K.

PY - 2011/4/27

Y1 - 2011/4/27

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=79953248412&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.08.052

DO - 10.1016/j.tetlet.2010.08.052

M3 - Article

SN - 0040-4039

VL - 52

SP - 2024

EP - 2027

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -