Literature DB >> 25514017

A concise total synthesis of breitfussin A and B.

Sunil Kumar Pandey1, Yngve Guttormsen, Bengt Erik Haug, Christian Hedberg, Annette Bayer.   

Abstract

The first total synthesis of breitfussin A and B is described. The approach features two palladium-catalyzed cross-couplings installing the indole and pyrrole onto the oxazole core and selective lithiation/iodination of a common indole-oxazole fragment providing 2,4-diiodinated or 2-iodinated oxazoles as potential precursors for breitfussin A and B, respectively. An unexpected acid promoted deiodination was utilized in the synthesis of breitfussin B. Comparison of the synthetic material with previously reported spectral data of isolated breitfussin A and B verified the structure of the breitfussin framework.

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Year:  2014        PMID: 25514017     DOI: 10.1021/ol503348n

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

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2.  Total Synthesis of Tambromycin Enabled by Indole C-H Functionalization.

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Journal:  Mar Drugs       Date:  2021-09-10       Impact factor: 5.118

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Journal:  Mar Drugs       Date:  2017-02-23       Impact factor: 5.118

5.  Unequivocal structure confirmation of a breitfussin analog by anisotropic NMR measurements.

Authors:  Ikenna E Ndukwe; Yu-Hong Lam; Sunil K Pandey; Bengt E Haug; Annette Bayer; Edward C Sherer; Kirill A Blinov; R Thomas Williamson; Johan Isaksson; Mikhail Reibarkh; Yizhou Liu; Gary E Martin
Journal:  Chem Sci       Date:  2020-09-21       Impact factor: 9.825

Review 6.  An Overview of Bioactive 1,3-Oxazole-Containing Alkaloids from Marine Organisms.

Authors:  Jinyun Chen; Sunyan Lv; Jia Liu; Yanlei Yu; Hong Wang; Huawei Zhang
Journal:  Pharmaceuticals (Basel)       Date:  2021-12-06
  6 in total

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