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

Article


Kotiw, Michael and Davis, Rohan A.. 2005. "Synthesis of the fungal natural product (-)-xylariamide A." Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry. 46 (31), pp. 5199-5201. https://doi.org/10.1016/j.tetlet.2005.05.114
Article Title

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

ERA Journal ID1602
Article CategoryArticle
AuthorsKotiw, Michael (Author) and Davis, Rohan A. (Author)
Journal TitleTetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry
Journal Citation46 (31), pp. 5199-5201
Number of Pages3
Year2005
Place of PublicationUnited Kingdom
ISSN0040-4039
1873-3581
Digital Object Identifier (DOI)https://doi.org/10.1016/j.tetlet.2005.05.114
Web Address (URL)https://www.sciencedirect.com/science/article/pii/S004040390501172X
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.

Keywordssynthesis; natural product; (-)-Xylariamide A; (+)-Xylariamide A; (-)-Dechloroxylariamide A; N,O-Bis(trimethylsily)acetamide
Contains Sensitive ContentDoes not contain sensitive content
ANZSRC Field of Research 2020310705. Mycology
340502. Natural products and bioactive compounds
340503. Organic chemical synthesis
Public Notes

File reproduced in accordance with the copyright policy of the publisher/author.

Byline AffiliationsDepartment of Biological and Physical Sciences
Griffith University
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