Synthesis of the fungal natural product (-)-xylariamide A

Davis, RA; Kotiw, M

doi:10.1016/j.tetlet.2005.05.114

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Author(s)

Davis, RA

Kotiw, M

Griffith University Author(s)

Davis, Rohan A.

Year published

2005

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Abstract

The first synthesis of the fungal natural product (-)-xylariamide A 1 is reported. N,O-Bis(trimethylsilyl)acetamide induced coupling of D-tyrosine with (E)-but-2-enedioic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester 5 produced the dechloro natural product 6, which was subsequently monochlorinated using oxone and KCl to yield synthetic 1. (-)-Xylariamide A 1, (+)-xylariamide A 2 and (-)-dechloroxylariamide A 6 displayed no cytotoxic or antimicrobial activity.The first synthesis of the fungal natural product (-)-xylariamide A 1 is reported. N,O-Bis(trimethylsilyl)acetamide induced coupling of D-tyrosine with (E)-but-2-enedioic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester 5 produced the dechloro natural product 6, which was subsequently monochlorinated using oxone and KCl to yield synthetic 1. (-)-Xylariamide A 1, (+)-xylariamide A 2 and (-)-dechloroxylariamide A 6 displayed no cytotoxic or antimicrobial activity.
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Journal Title

Tetrahedron Letters

Volume

Publisher URI

http://www.sciencedirect.com/science/journal/00404039

DOI

https://doi.org/10.1016/j.tetlet.2005.05.114

Copyright Statement

© 2005 Elsevier : Reproduced in accordance with the copyright policy of the publisher : This journal is available online - use hypertext links. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher.

Subject

Medicinal and biomolecular chemistry

Organic chemistry

Publication URI

http://hdl.handle.net/10072/4981

Collection

Journal articles