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 DielsāAlder cycloaddition reaction as the key step. A Kumada cross-coupling reaction on a 1-chloroisoquinoline intermediate provided the natural product.