Issue 39, 2009
From the journal:

Chemical Communications

Enantio- and stereoselective route to the phoslactomycin family of antibiotics: formal synthesis of (+)-fostriecin and (+)-phoslactomycin B†

Shaheen M. Sarkar,a   Everlyne N. Wanzala,a   Setsuya Shibahara,a   Keisuke Takahashi,a   Jun Ishiharaa  and  Susumi Hatakeyama*a  

* Corresponding authors

a Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan
E-mail: susumi@nagasaki-u.ac.jp
Fax: +81-95-819-2426
Tel: +81-95-819-2426

Abstract

A general methodology applicable for the synthesis of the phoslactomycin family of antibiotics, potent and selective protein phosphatase inhibitors, has been developed starting from a β-isocupreidine-catalyzed asymmetric Baylis–Hillman reaction of 3-(4-methoxybenzyloxy)propanal with hexafluoroisopropyl acrylate, and thereby formal syntheses of (+)-fostriecin and (+)-phoslactomycin B have been accomplished.

Graphical abstract: Enantio- and stereoselective route to the phoslactomycin family of antibiotics: formal synthesis of (+)-fostriecin and (+)-phoslactomycin B

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Article information

DOI
https://doi.org/10.1039/B912267B
Article type
Communication
Submitted
22 Jun 2009
Accepted
22 Jul 2009
First published
10 Aug 2009

Chem. Commun., 2009, 5907-5909

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Enantio- and stereoselective route to the phoslactomycin family of antibiotics: formal synthesis of (+)-fostriecin and (+)-phoslactomycin B

S. M. Sarkar, E. N. Wanzala, S. Shibahara, K. Takahashi, J. Ishihara and S. Hatakeyama, Chem. Commun., 2009, 5907 DOI: 10.1039/B912267B

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