Literature DB >> 11262141

The first total synthesis of +-ratjadone.

U Bhatt1, M Christmann, M Quitschalle, E Claus, M Kalesse.   

Abstract

The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis of structural analogues for biological target identification.

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Year:  2001        PMID: 11262141     DOI: 10.1021/jo005768g

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 in total

1.  New Mandelalides Expand a Macrolide Series of Mitochondrial Inhibitors.

Authors:  Mohamad Nazari; Jeffrey D Serrill; Xuemei Wan; Minh H Nguyen; Clemens Anklin; David A Gallegos; Amos B Smith; Jane E Ishmael; Kerry L McPhail
Journal:  J Med Chem       Date:  2017-09-07       Impact factor: 7.446

2.  Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy.

Authors:  Minh H Nguyen; Masashi Imanishi; Taichi Kurogi; Xuemei Wan; Jane E Ishmael; Kerry L McPhail; Amos B Smith
Journal:  J Org Chem       Date:  2018-02-26       Impact factor: 4.354

3.  The nuclear export inhibitor aminoratjadone is a potent effector in extracellular-targeted drug conjugates.

Authors:  Philipp Klahn; Verena Fetz; Antje Ritter; Wera Collisi; Bettina Hinkelmann; Tatjana Arnold; Werner Tegge; Katharina Rox; Stephan Hüttel; Kathrin I Mohr; Joachim Wink; Marc Stadler; Josef Wissing; Lothar Jänsch; Mark Brönstrup
Journal:  Chem Sci       Date:  2019-04-15       Impact factor: 9.825

4.  Cobalt-Catalyzed E-Selective Isomerization of Alkenes with a Phosphine-Amido-Oxazoline Ligand.

Authors:  Hongmei Liu; Cheng Cai; Yanghao Ding; Jianhui Chen; Bosheng Liu; Yuanzhi Xia
Journal:  ACS Omega       Date:  2020-05-12

5.  Ni-catalyzed regio- and stereo-defined intermolecular cross-electrophile dialkylation of alkynes without directing group.

Authors:  Yi-Zhou Zhan; Nan Xiao; Wei Shu
Journal:  Nat Commun       Date:  2021-02-10       Impact factor: 14.919

6.  Total Synthesis of (-)-Mandelalide A Exploiting Anion Relay Chemistry (ARC): Identification of a Type II ARC/CuCN Cross-Coupling Protocol.

Authors:  Minh H Nguyen; Masashi Imanishi; Taichi Kurogi; Amos B Smith
Journal:  J Am Chem Soc       Date:  2016-03-08       Impact factor: 15.419

  6 in total

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