Journal
TETRAHEDRON
Volume 62, Issue 51, Pages 12017-12024Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.09.077
Keywords
convolutamydine A; aldol reaction; organocatalysis; DFT calculations
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The first total synthesis of (R)-convolutamydine A has been achieved by the organocatalytic addition of acetone to 4,6-dibro-moisatin. The absolute configuration was determined by single crystal X-ray diffraction. DFT studies were used to model the transition states for the aldol reaction and equilibrium geometries of the post-aldol reaction intermediates. The DFT study revealed that the aldol bond forming reaction was considerably endothermic. (c) 2006 Elsevier Ltd. All rights reserved.
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