Total synthesis and stereochemical reassignment of (±)-indoxamycin B

Angewandte Chemie
Oliver F Jeker, Erick M Carreira

Abstract

Revised version: the first total synthesis of indoxamycin B leads to a stereochemical reassignment of the natural product. The synthetic route features an efficient carboannulation sequence to rapidly access the dihydroindenone system. Moreover, a series of Au(I)-catalyzed transformations served in the construction of the sterically congested core framework.

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Citations

Jul 28, 2013·Journal of the American Chemical Society·John T S YeomanSarah E Reisman
Jan 7, 2014·Natural Product Reports·John W BluntMichèle R Prinsep
Dec 23, 2015·Organic Letters·Stefan A Ruider, Erick M Carreira
Feb 4, 2016·Natural Product Reports·John W BluntMichèle R Prinsep
Mar 19, 2013·Biotechnology Advances·Saradavey Vinothkumar, P S Parameswaran
Jul 28, 2016·Chemical Reviews·Steven W M CrossleyRyan A Shenvi
Jan 26, 2017·Organic Letters·Yushi HirataToshio Nishikawa
May 23, 2017·Organic Letters·Nan ZhengZhen Yang
Jun 7, 2014·Chemistry : a European Journal·Lutz F TietzeBernd Waldecker
Jan 13, 2016·Chemical Society Reviews·Reinhard W Hoffmann
Jan 27, 2015·Natural Product Reports·John W BluntMichèle R Prinsep
Nov 14, 2015·Chemistry : a European Journal·Jonathan M PercyDavid J Hirst
Sep 30, 2014·Chemistry : a European Journal·Chi HeHanfeng Ding
Feb 19, 2013·Chemistry : a European Journal·Lutz F TietzeMaria Claudia Ochoa Campos
Mar 6, 2019·Angewandte Chemie·Naifeng HuGuangxin Liang
Nov 1, 2013·Angewandte Chemie·Chi HeHanfeng Ding
Jul 12, 2017·Angewandte Chemie·Helene Wolleb, Erick M Carreira
Nov 20, 2012·Angewandte Chemie·Nikolas Huwyler, Erick M Carreira
Sep 10, 2020·Angewandte Chemie·Hong-Xiu HuangYong Qin
Jan 22, 2021·Angewandte Chemie·Anup BhuniaArmido Studer
May 6, 2021·Chemistry : a European Journal·Robert J HarrisRoss A Widenhoefer
May 23, 2013·The Journal of Organic Chemistry·Baudouin GerardLisa A Marcaurelle
Apr 25, 2020·Organic Letters·Hui ShaoYong-Qiang Tu
Apr 27, 2016·Journal of the American Chemical Society·Xuerong YuTuoping Luo
Apr 7, 2015·Chemical Reviews·Ruth Dorel, Antonio M Echavarren
Jan 23, 2020·Journal of the American Chemical Society·Jin WangXiaoguang Lei
Feb 25, 2020·The Journal of Organic Chemistry·Misaki NikiToshio Nishikawa
Nov 3, 2020·Accounts of Chemical Research·Weilong LiuXiaoguang Lei

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