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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Official URL: http://www.sciencedirect.com/science/journal/00404039
Identification Number or DOI: doi: 10.1016/j.tetlet.2005.05.114
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.
| Item Type: | Article (Commonwealth Reporting Category C) |
|---|---|
| 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. |
| Uncontrolled Keywords: | synthesis; natural product; (-)-Xylariamide A; (+)-Xylariamide A; (-)-Dechloroxylariamide A; N,O-Bis(trimethylsily)acetamide |
| Fields of Research (FOR2008): | 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 |
| Subjects: | 270000 Biological Sciences > 270300 Microbiology > 270305 Mycology 270000 Biological Sciences |
| Socio-Economic Objective (SEO2008): | E Expanding Knowledge > 97 Expanding Knowledge > 970103 Expanding Knowledge in the Chemical Sciences |
| ID Code: | 449 |
| Deposited By: | |
| Deposited On: | 11 Oct 2007 10:21 |
| Last Modified: | 06 Feb 2012 11:38 |
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