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Synthesis 2007(18): 2894-2900  
DOI: 10.1055/s-2007-983873
PAPER
© Georg Thieme Verlag Stuttgart · New York

First Chemical Synthesis of the Antiviral Agents S2502 and S2507

Karsten Krohn*, Krisztina Vukics
Department of Chemistry, University of Paderborn, Warburger Straße 100, 33098 Paderborn, Germany
Fax: +49(5251)603245; e-Mail: k.krohn@uni-paderborn.de;
Further Information

Publication History

Received 23 April 2007
Publication Date:
29 August 2007 (online)

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Abstract

The first chemical synthesis of S2502 and S2507, highly active antiviral, bioengineered fermentation products, has been achieved using a biomimetic approach. Key steps of the synthesis involved addition of the dianion of acetylacetone to isochromene 10, followed by boron tribromide mediated simultaneous methyl ether cleavage, E/Z isomerization, cyclization, and transesterification/saponification to give S2502 (7) and S2507 (8). In a related reaction, the analogous esters 20 and 21 were obtained by treatment of isochromene 10 with the dianion of methyl acetoacetate, followed by boron tribromide treatment.

Key words

antiviral compounds - dianion condensation - biomimetic synthesis - boron tribromide - E/Z-isomerization

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1

Current address: Gedeon Richter Ltd. Budapest 10, P.O.B. 27, 1475 Hungary.

18

PM3 (Parameterization Method 3) calculations, Gaussian program package.

19

The spectroscopic data of the synthetic products were in agreement with the published data for the microbial products. No information on the stereochemistry and melting points of the fermentation products 7 and 8 is given in references 12-14.