@article{enamorado_ondachi_comins_2010, title={A Five-Step Synthesis of (S)-Macrostomine from (S)-Nicotine}, volume={12}, ISSN={["1523-7052"]}, DOI={10.1021/ol101887b}, abstractNote={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.}, number={20}, journal={ORGANIC LETTERS}, author={Enamorado, Monica F. and Ondachi, Pauline W. and Comins, Daniel L.}, year={2010}, month={Oct}, pages={4513–4515} } @article{ondachi_comins_2010, title={Synthesis of Fused-Ring Nicotine Derivatives from (S)-Nicotine}, volume={75}, ISSN={["0022-3263"]}, DOI={10.1021/jo9026929}, abstractNote={The synthesis of novel fused-ring bicyclic (4-6) and tricyclic (7-10) nicotine derivatives from natural (S)-nicotine are described. Enantiopure bicyclic dioxino, dihydrofuro, and dihydropyranol nicotine derivatives as well as tricylic benzofuro and benzopyran derivatives were synthesized from simple alkoxy or halonicotine intermediates. Attempts to synthesize furonicotines (11, 12) resulted in formation of the furonicotine dimers 42 and 49.}, number={5}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Ondachi, Pauline W. and Comins, Daniel L.}, year={2010}, month={Mar}, pages={1706–1716} } @article{ondachi_comins_2008, title={Synthesis and regioselective substitution of C-6 alkoxy derivatives of (S)-nicotine}, volume={49}, ISSN={["0040-4039"]}, DOI={10.1016/j.tetlet.2007.11.041}, abstractNote={Enantiopure (S)-6-alkoxynicotine derivatives have been synthesized in two steps from (S)-nicotine via (S)-6-iodonicotine. Deprotonation and substitution at the C-5 position of the pyridine ring of (S)-6-methoxynicotine were achieved using mesityllithium as the base at 0 °C. Conditions for the C-4 lithiation/substitution of (S)-6-isopropoxynicotine and (S)-5-chloro-6-methoxynicotine were also developed.}, number={3}, journal={TETRAHEDRON LETTERS}, author={Ondachi, Pauline W. and Comins, Daniel L.}, year={2008}, month={Jan}, pages={569–572} }