Literature DB >> 20225835

Total synthesis of kendomycin featuring intramolecular Dötz benzannulation.

Kyosuke Tanaka1, Masahito Watanabe, Kodai Ishibashi, Hiroshi Matsuyama, Yoko Saikawa, Masaya Nakata.   

Abstract

One-step formation of the ansa-skeleton realized the synthesis of kendomycin, an ansa-type quinone methide. The Fischer carbene complex derived from the ansa-chain portion was subjected to the intramolecular Dotz benzannulation to afford the desired oxametacyclophane with exclusive regioselectivity. Subsequent Claisen rearrangement, ortho oxidation of the resulting phenol derivative, and mild transformation from p-quinone to p-quinone methide on a silica gel plate furnished kendomycin.

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Year:  2010        PMID: 20225835     DOI: 10.1021/ol100229f

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


  2 in total

Review 1.  Strategies for construction of the all-carbon macrocyclic skeleton of the ansamycin antibiotic-kendomycin.

Authors:  Shu Xu; Hirokazu Arimoto
Journal:  J Antibiot (Tokyo)       Date:  2016-02-10       Impact factor: 2.649

2.  Investigations to the Antibacterial Mechanism of Action of Kendomycin.

Authors:  Yasser A Elnakady; Indranil Chatterjee; Markus Bischoff; Manfred Rohde; Michaele Josten; Hans-Georg Sahl; Mathias Herrmann; Rolf Müller
Journal:  PLoS One       Date:  2016-01-21       Impact factor: 3.240

  2 in total

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