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

Davis, Rohan; Kotiw, Michael

doi:10.1016/j.tetlet.2005.05.114

View/Open

29800_1.pdf (103.9Kb)

Author

Davis, Rohan

Kotiw, Michael

Year published

2005

Metadata

Show full item record

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.
View less >

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.

Publication URI

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

Collection

Journal articles