10.1021/ol101887b.s001 Monica F. Enamorado Monica F. Enamorado Pauline W. Ondachi Pauline W. Ondachi Daniel L. Comins Daniel L. Comins A Five-Step Synthesis of (<i>S</i>)-Macrostomine from (<i>S</i>)-Nicotine American Chemical Society 2010 nicotine pyridyne Kumada cycloaddition Diel synthesis chloroisoquinoline Synthesi 2010-10-15 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/A_Five_Step_Synthesis_of_i_S_i_Macrostomine_from_i_S_i_Nicotine/2721790 A concise synthesis of (<i>S</i>)-macrostomine has been accomplished in five steps from natural nicotine in 19% overall yield via a pyridyne Dielsāˆ’Alder cycloaddition reaction as the key step. A Kumada cross-coupling reaction on a 1-chloroisoquinoline intermediate provided the natural product.