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Issue 99, 2014
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A new route to platencin via decarboxylative radical cyclization

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Abstract

A new approach to platencin, a potent antibiotic isolated from Streptomyces platensis, has been established. The highly congested tricyclic core of the natural product was successfully constructed by decarboxylative radical cyclization of an alkynyl silyl ester with Pb(OAc)4 in the presence of pyridine in refluxing 1,4-dioxane. The key decarboxylation, which likely takes place via lead(IV) esterification followed by carbon-centered radical generation and subsequent capture of the radical with a triple bond, allows the rapid construction of the twisted polycyclic system.

Graphical abstract: A new route to platencin via decarboxylative radical cyclization

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Article information


Submitted
16 Sep 2014
Accepted
23 Oct 2014
First published
31 Oct 2014

Chem. Commun., 2014,50, 15706-15709
Article type
Communication

A new route to platencin via decarboxylative radical cyclization

G. A. I. Moustafa, Y. Saku, H. Aoyama and T. Yoshimitsu, Chem. Commun., 2014, 50, 15706
DOI: 10.1039/C4CC07316A

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