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

Kotiw, Michael and Davis, Rohan A. (2005) Synthesis of the fungal natural product (-)-xylariamide A. Tetrahedron Letters, 46 (31). pp. 5199-5201. ISSN 0040-4039

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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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Item Type: Article (Commonwealth Reporting Category C)
Refereed: Yes
Item Status: Live Archive
Additional Information: Copyright 2005 Elsevier This is the authors' version of the work. It is posted here with permission of the publisher for your personal use. No further distribution is permitted. If your Library has a subscription to this journal, you may also be able to access the published version via hypertext links above.
Faculty / Department / School: Historic - Faculty of Sciences - Department of Biological and Physical Sciences
Date Deposited: 11 Oct 2007 00:21
Last Modified: 02 Jul 2013 22:32
Uncontrolled Keywords: synthesis; natural product; (-)-Xylariamide A; (+)-Xylariamide A; (-)-Dechloroxylariamide A; N,O-Bis(trimethylsily)acetamide
Fields of Research : 06 Biological Sciences > 0605 Microbiology > 060505 Mycology
03 Chemical Sciences > 0305 Organic Chemistry > 030502 Natural Products Chemistry
03 Chemical Sciences > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis
Socio-Economic Objective: E Expanding Knowledge > 97 Expanding Knowledge > 970103 Expanding Knowledge in the Chemical Sciences
Identification Number or DOI: 10.1016/j.tetlet.2005.05.114

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