Issue 42, 2008
From the journal:

Chemical Communications

Internal amide-triggered cycloaromatization of maduropeptin-like nine-membered enediyne

Yutaro Norizuki,a   Kazuo Komano,a   Itaru Sato*b  and  Masahiro Hirama*a  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, Japan
E-mail: hirama@mail.tains.tohoku.ac.jp
Fax: +81-22-795-6566

b Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Japan
E-mail: isato@mail.tains.tohoku.ac.jp

Abstract

In the Masamune–Bergman cyclization of a nine-membered non-conjugated enediyne with an internal, maduropeptin-like nucleophile, the exocyclic alkene migrated to form the nine-membered conjugated enediyne, triggered by the intramolecular addition of the amide group; final aromatized products showed up to 85% yield.

Graphical abstract: Internal amide-triggered cycloaromatization of maduropeptin-like nine-membered enediyne

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Article information

DOI
https://doi.org/10.1039/B811355F
Article type
Communication
Submitted
03 Jul 2008
Accepted
29 Jul 2008
First published
15 Sep 2008

Chem. Commun., 2008, 5372-5374

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Internal amide-triggered cycloaromatization of maduropeptin-like nine-membered enediyne

Y. Norizuki, K. Komano, I. Sato and M. Hirama, Chem. Commun., 2008, 5372 DOI: 10.1039/B811355F

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