Issue 60, 2013

Convergent de novo synthesis of vineomycinone B2methyl ester

Abstract

An efficient de novo synthesis of vineomycinone B2 methyl ester has been achieved. The longest linear route required only 14 steps from achiral commercially available starting materials (4.0% overall yield). The key transformations included the de novo asymmetric synthesis of two key fragments, which were joined by a convergent late stage Suzuki's glycosylation for the construction of the aryl β-C-glycoside. A subsequent BBr3 one-pot debenzylation, demethylation and air oxidation provided vineomycinone B2 methyl ester.

Graphical abstract: Convergent de novo synthesis of vineomycinone B2 methyl ester

Supplementary files

Article information

Article type
Communication
Submitted
29 May 2013
Accepted
12 Jun 2013
First published
13 Jun 2013

Chem. Commun., 2013,49, 6806-6808

Convergent de novo synthesis of vineomycinone B2 methyl ester

Q. Chen, Y. Zhong and G. A. O'Doherty, Chem. Commun., 2013, 49, 6806 DOI: 10.1039/C3CC44050H

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