Total synthesis of the leucosceptroid family of natural products

Journal of the American Chemical Society
Cedric L Hugelshofer, Thomas Magauer

Abstract

A highly efficient strategy enabled the asymmetric total synthesis of 15 antifeedant leucosceptroid natural products. The advanced tricyclic core, available in gram quantity, served as the pivotal intermediate for the preparation of norleucosceptroids B, C, F, and G and leucosceptroids A, B, G, I, J, L, and M. Additionally, the bioinspired oxidative transformation of leucosceptroid A to leucosceptroids C, K, O, and P using singlet oxygen supports the hypothesis that leucosceptroids A and B are most likely the biogenetic precursors of all other members of this natural product family.

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Citations

Apr 30, 2016·Chemical Reviews·Ashwini A Ghogare, Alexander Greer
May 10, 2016·Journal of the American Chemical Society·Cedric L Hugelshofer, Thomas Magauer
Jul 28, 2016·Chemical Reviews·Steven W M CrossleyRyan A Shenvi
Feb 9, 2017·The Journal of Organic Chemistry·Yu BaiMingji Dai
Feb 22, 2017·Journal of the American Chemical Society·Hong-Dong Hao, Dirk Trauner
Mar 16, 2017·Chemical Reviews·Zachary G BrillThomas J Maimone
May 24, 2017·Organic & Biomolecular Chemistry·Henry P PepperJonathan H George
Jun 16, 2016·Chemistry : a European Journal·Lisa Gerstmann, Markus Kalesse
Sep 8, 2016·Chemistry : a European Journal·Cedric L Hugelshofer, Thomas Magauer
Feb 23, 2017·Angewandte Chemie·Hiu C LamJonathan H George
Apr 4, 2017·Angewandte Chemie·Wei ZhangRongbiao Tong
Dec 6, 2016·Organic & Biomolecular Chemistry·Cedric L Hugelshofer, Thomas Magauer
Jul 5, 2017·Chemical Society Reviews·Magnus W P Bebbington
Jun 24, 2017·Chemical Reviews·Bin MaoBen L Feringa
Sep 15, 2018·Natural Product Reports·Yuye ChenJing Xu
Jun 21, 2018·Natural Product Reports·Kaiqing MaMingji Dai
Nov 11, 2016·Beilstein Journal of Organic Chemistry·Juliane AdrianChristian B W Stark
Aug 26, 2016·Beilstein Journal of Organic Chemistry·Ivan A YaremenkoAlexander O Terent'ev
Sep 18, 2020·Chemical Communications : Chem Comm·Evgeniya SemenovaAlexander J Grenning
May 29, 2020·Beilstein Journal of Organic Chemistry·Rodrigo Costa E SilvaKleber Thiago de Oliveira
Jan 16, 2021·Accounts of Chemical Research·Yang Gao, Dawei Ma
Apr 8, 2021·The Journal of Organic Chemistry·Shu-Xi JingSheng-Hong Li
Nov 1, 2018·The Journal of Organic Chemistry·Shengling XieJing Xu
Mar 9, 2018·Chemical Reviews·Lei LiYanxing Jia
Apr 25, 2019·Journal of the American Chemical Society·Zhiyao ZhouScott A Snyder
Jan 8, 2021·The Journal of Organic Chemistry·Peng SunGuangxin Liang
Dec 19, 2019·The Journal of Organic Chemistry·Aaron J DayJonathan H George
Jan 6, 2021·Journal of the American Chemical Society·Franz-Lucas HautThomas Magauer

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