@article{tsukanov_marks_comins_2016, title={Studies toward the Synthesis of Lepadiformine A}, volume={81}, ISSN={["0022-3263"]}, DOI={10.1021/acs.joc.6b01514}, abstractNote={Herein is described an original approach to access a tricyclic framework of the lepadiformine-type alkaloids. A Grignard/N-acylpyridinium salt reaction of a 4-methoxytetrahydroquinoline is the key carbon-carbon bond-forming step that was used to establish the desired absolute stereochemistry at the C2 position of the target alkaloid. The synthesis features an allylation reaction with an N-acyliminium ion to set the C10 quaternary stereocenter, a mild dissolving-metal cleavage of hindered phenyl carbamates, and an aminoiodocyclization to form the pyrrolidine ring. While this route does not provide the correct C10 stereochemistry, it showcases an efficient method to build analogues with the ring system of this class of alkaloids in 11 steps overall.}, number={21}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Tsukanov, Sergey V. and Marks, Lucas R. and Comins, Daniel L.}, year={2016}, month={Nov}, pages={10433–10443} } @article{tsukanov_comins_2014, title={Total Synthesis of Alkaloid 205B}, volume={79}, ISSN={["0022-3263"]}, DOI={10.1021/jo501415r}, abstractNote={Concise and highly stereocontrolled total syntheses of racemic and enantiopure frog alkaloid 205B (1) were accomplished in 11 steps from 4-methoxypyridines 6 and 7 in overall yields of 8 and 8%, respectively. The assembly of the core of the natural product relies on a stereoselective Tsuji–Trost allylic amination reaction and a ring-closing metathesis. The synthesis features the use of an N-acylpyridinium salt reaction to introduce the first stereocenter and an unprecedented trifluoroacetic anhydride-mediated addition of an allylstannane to a vinylogous amide with complete facial selectivity. Deoxygenation of the C4 ketone proved difficult but was accomplished via a modified Barton–McCombie reaction in the presence of a catalytic amount of diphenyl diselenide.}, number={19}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Tsukanov, Sergey V. and Comins, Daniel L.}, year={2014}, month={Oct}, pages={9074–9085} } @article{tsukanov_comins_2011, title={Concise Total Synthesis of the Frog Alkaloid (-)-205B}, volume={50}, ISSN={["1433-7851"]}, DOI={10.1002/anie.201103596}, abstractNote={Highly stereocontrolled: The total synthesis of frog alkaloid (−)-205B features a chiral N-acylpyridinium salt reaction and an unprecedented trifluoroacetic anhydride mediated addition of an allylstannane to a vinylogous amide. The core was assembled using a Tsuji–Trost allylic amination reaction and a ring-closing metathesis. TIPS=triisopropylsilyl. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.}, number={37}, journal={ANGEWANDTE CHEMIE-INTERNATIONAL EDITION}, author={Tsukanov, Sergey V. and Comins, Daniel L.}, year={2011}, pages={8626–8628} }