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Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: synthesis of the tricyclic core of martinellic acid.
|Publication Type||Journal Article|
|Authors||Ng, PY, Masse CE, and Shaw JT|
|Abstract||Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce gamma-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-pi repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.|
|Year of Publication||2006|
|Date Published (YYYY/MM/DD)||2006/08/31|