Issue 3, 2014
From the journal:

Chemical Science

Stereoselective synthesis of spirotryprostatin A†

Katsushi Kitahara,a   Jun Shimokawa‡a  and  Tohru Fukuyama‡*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
E-mail: fukuyama@mol.f.u-tokyo.ac.jp
Fax: +81-3-5802-8694
Tel: +81-3-5841-4777

Abstract

The asymmetric synthesis of spirotryprostatin A was achieved by employing an intramolecular Heck reaction to introduce the quaternary spiro center. The stereochemistry of the reaction was controlled by a tethering system, which was selectively introduced by taking advantage of the unique and as yet mysterious characteristics of the cyclo-(Pro–Pro) diketopiperazine moiety.

Graphical abstract: Stereoselective synthesis of spirotryprostatin A

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Article information

DOI
https://doi.org/10.1039/C3SC52525B
Article type
Edge Article
Submitted
07 Sep 2013
Accepted
11 Oct 2013
First published
14 Oct 2013

Chem. Sci., 2014,5, 904-907

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Stereoselective synthesis of spirotryprostatin A

K. Kitahara, J. Shimokawa and T. Fukuyama, Chem. Sci., 2014, 5, 904 DOI: 10.1039/C3SC52525B

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