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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2OB25111F
Article type
Paper
Submitted
15 1 2012
Accepted
09 3 2012
First published
12 3 2012

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements