Issue 30, 2012
From the journal:

Organic & Biomolecular Chemistry

Platinum catalyzed 7-endocyclization of internal alkynyl amides and its application to synthesis of the caprazamycin core†‡

Chihiro Tsukano,a   Shinsuke Yokouchi,a   Anne-Lise Girard,a   Toshifumi Kuribayashi,a   Shota Sakamoto,a   Taro Enomotoa  and  Yoshiji Takemoto*a  

* Corresponding authors

a 46-29 Yoshida, Sakyo-ku, Kyoto, Japan
E-mail: takemoto@pharm.kyoto-u.ac.jp
Fax: +81 75 753 4569
Tel: +81 75 753 4528

Abstract

The scope and limitations of the platinum catalyzed 7-endo cyclization of internal alkynyl amides were investigated. Substitution of the alkyne with an aryl group gave better results, presumably because it stabilized the transition state. Applying the reaction to a secondary amide, the caprazamycin core was successfully synthesized from commercially available material in eight steps.

Graphical abstract: Platinum catalyzed 7-endo cyclization of internal alkynyl amides and its application to synthesis of the caprazamycin core

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Article information

DOI
https://doi.org/10.1039/C2OB25111F
Article type
Paper
Submitted
15 jan 2012
Accepted
09 mar 2012
First published
12 mar 2012

Org. Biomol. Chem., 2012,10, 6074-6086

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Platinum catalyzed 7-endo cyclization of internal alkynyl amides and its application to synthesis of the caprazamycin core

C. Tsukano, S. Yokouchi, A. Girard, T. Kuribayashi, S. Sakamoto, T. Enomoto and Y. Takemoto, Org. Biomol. Chem., 2012, 10, 6074 DOI: 10.1039/C2OB25111F

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