Synthesis of the fungal natural product (-)-xylariamide A
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Kotiw, M
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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.
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Tetrahedron Letters
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46
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© 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.
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Medicinal and biomolecular chemistry
Organic chemistry