Literature DB >> 23330661

Enantioselective total syntheses and absolute configuration of JBIR-02 and Mer-A2026B.

Johannes Hoecker1, Karl Gademann.   

Abstract

The first total syntheses of the piericidin related natural products Mer-A2026B and JBIR-02 are reported. Key features of the synthetic approach involve an Ir-catalyzed one-pot C-H activation/oxidation procedure for the preparation of the hydroxypyridine, a vinylogous Mukaiyama aldol reaction, and a final Negishi cross-coupling of an advanced pyridine derivative with an allylic side chain precursor. In addition, the absolute configuration of Mer-A2026B (9R,10R) and JBIR-02 (9R,10R) was established.

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Year:  2013        PMID: 23330661     DOI: 10.1021/ol303502a

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


  5 in total

Review 1.  Negishi coupling: an easy progress for C-C bond construction in total synthesis.

Authors:  Majid M Heravi; Elaheh Hashemi; Niousha Nazari
Journal:  Mol Divers       Date:  2014-03-07       Impact factor: 2.943

Review 2.  The unique chemistry and biology of the piericidins.

Authors:  Xuefeng Zhou; William Fenical
Journal:  J Antibiot (Tokyo)       Date:  2016-06-15       Impact factor: 2.649

3.  Investigation of carbonyl amidation and O-methylation during biosynthesis of the pharmacophore pyridyl of antitumor piericidins.

Authors:  Wanlu Li; Wenyu Zhang; Yijia Cheng; Yaoyao Shen; Jianzhao Qi; Hou-Wen Lin; Yongjun Zhou
Journal:  Synth Syst Biotechnol       Date:  2022-05-10

Review 4.  Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis.

Authors:  Martin Cordes; Markus Kalesse
Journal:  Molecules       Date:  2019-08-22       Impact factor: 4.411

5.  Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica.

Authors:  Danny Geerdink; Jeffrey Buter; Teris A van Beek; Adriaan J Minnaard
Journal:  Beilstein J Org Chem       Date:  2014-04-02       Impact factor: 2.883

  5 in total

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