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The first total synthesis of (R)-convolutamydine A |
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| Authors: | Gianluigi Luppi Rodrigo J Corrêa Angelo C Pinto Quirinus B Broxterman Claudia Tomasini |
| Institution: | a Dipartimento di Chimica ‘G. Ciamician’—Alma Mater Studiorum Università di Bologna, Via Selmi 2, 40126 Bologna, Italy b Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, Ilha do Fundão, Bloco A, CT, Rio de Janeiro CEP 219450-900, Brazil c DSM Research, Life Science—Advanced Synthesis and Catalysis, PO Box 18, 6160 MD Geleen, The Netherlands |
| Abstract: | The first total synthesis of (R)-convolutamydine A has been achieved by the organocatalytic addition of acetone to 4,6-dibromoisatin. 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. |
| Keywords: | Convolutamydine A Aldol reaction Organocatalysis DFT calculations |
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