Application of the chiral base desymmetrisation of imides to the synthesis of the alkaloid jamtine and the antidepressant paroxetine |
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Authors: | Christopher D GillDaniel A Greenhalgh Nigel S Simpkins |
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Institution: | School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK |
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Abstract: | The synthesis of the alkaloid jamtine and the antidepressant paroxetine have been addressed by a strategy involving asymmetric desymmetrisation of prochiral imides by a chiral lithium amide base. A short reaction sequence, starting with a cyclohexane fused succinimide, led to the structures originally reported for the alkaloid jamtine and its derived N-oxide. The structures synthesised are shown not to correspond with those originally reported. A second sequence involves desymmetrisation of a 4-arylglutarimide, and provides a short enantioselective synthesis of the drug substance paroxetine. |
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Keywords: | asymmetric synthesis enantioselective enolisation chiral lithium amide base imides paroxetine jamtine |
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