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A Five-Step Synthesis of (S)-Macrostomine from (S)-Nicotine

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journal contribution
posted on 15.10.2010, 00:00 by Monica F. Enamorado, Pauline W. Ondachi, Daniel L. Comins
A concise synthesis of (S)-macrostomine has been accomplished in five steps from natural nicotine in 19% overall yield via a pyridyne Diels−Alder cycloaddition reaction as the key step. A Kumada cross-coupling reaction on a 1-chloroisoquinoline intermediate provided the natural product.