Oxidative 1,2- and 1,3-alkyl shift processes: developments and applications in synthesis

The Journal of Organic Chemistry
Kimiaka C GuérardSylvain Canesi

Abstract

Oxidative 1,2- and 1,3- alkyl shifts mediated by a hypervalent iodine reagent were performed on simple and inexpensive phenol derivatives. These transpositions enable rapid redesign of the main aromatic skeleton to generate good yields of highly functionalized scaffolds containing a prochiral dienone system, a quaternary carbon center connected to as many as four sp(2) centers, and a carbonyl functionality or precursor. An efficient enantioselective version of this process resulting in the formation of a challenging quaternary carbon center is also described. The products represent the central cores of several natural products having important bioactivities. As an illustration of the potential of this method, we describe the rapid synthesis of several functionalized polycyclic systems as well as a formal synthesis of acetylaspidoalbidine, a hexacyclic alkaloid belonging to the Aspidosperma family.

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Citations

Feb 11, 2016·Chemical Reviews·Akira Yoshimura, Viktor V Zhdankin
Dec 1, 2015·The Journal of Organic Chemistry·Zhuang ChenYanxing Jia
Jan 21, 2015·Frontiers in Chemistry·Gaëtan MaertensSylvain Canesi
Aug 12, 2016·Journal of the American Chemical Society·Kolby L White, Mohammad Movassaghi
Apr 14, 2017·Organic & Biomolecular Chemistry·Elsa Deruer, Sylvain Canesi
Jan 23, 2016·Chemistry : a European Journal·Michael BrownThomas Wirth
Jun 22, 2016·Organic & Biomolecular Chemistry·Gaëtan MaertensSylvain Canesi
Jul 8, 2015·Natural Product Reports·Minoru IshikuraSatoshi Hibino
Aug 3, 2019·Organic & Biomolecular Chemistry·I F Dempsey HyattCyrus Mowdawalla
Jun 6, 2019·Nature Communications·Wan Shin KimGlenn C Micalizio
Apr 3, 2015·Chemistry : a European Journal·Guillaume JacquemotSylvain Canesi
Oct 13, 2015·Chemistry : a European Journal·Kimiaka C GuérardSylvain Canesi
May 2, 2014·Chemistry : a European Journal·Marc-André BeaulieuSylvain Canesi
Mar 24, 2016·Chemistry : a European Journal·Gaetan Maertens, Sylvain Canesi
Nov 4, 2020·Chemical Communications : Chem Comm·Beibei ZhangYunfei Du
Feb 4, 2021·Accounts of Chemical Research·Karina M Hugentobler, Erick M Carreira
Dec 9, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Nengzhong Wang, Xuefeng Jiang
Aug 8, 2012·The Journal of Organic Chemistry·Guillaume Jacquemot, Sylvain Canesi
Nov 6, 2018·The Journal of Organic Chemistry·Ayumi WatanabeMasanobu Uchiyama
Oct 18, 2013·The Journal of Organic Chemistry·Shao-Xiong ZhangZhi-Hui Shao
Mar 15, 2015·Journal of the American Chemical Society·Ji-Yuan DuChun-An Fan
Aug 21, 2014·The Journal of Organic Chemistry·Chloé L'HommeSylvain Canesi
Nov 10, 2018·Journal of the American Chemical Society·Matthieu J R RichterErick M Carreira
Dec 8, 2021·Organic & Biomolecular Chemistry·Chaofei WuJun Jiang

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