Isolation and Structure Elucidation of the New Fungal Metabolite (-)-Xylariamide A

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Davis, RA
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2005
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Abstract

Chemical investigations of the terrestrial microfungus Xylaria sp. have afforded the new natural product (-)-xylariamide A (1). The gross structure of 1 was determined by interpretation of 1D and 2D NMR, UV, IR and MS data. Confirmation of the structure and the absolute stereochemistry of 1 were determined by the total synthesis of (+)-xylariamide A (2). Synthetic 2 was produced by N,O-bis(trimethylsilyl)acetamide induced coupling of 3-chloro-L-tyrosine (3) with (E)-but-2-enedioic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester (4). Optical rotation comparison of 1 with 2 indicated that the natural product (1) contained 3-chloro-D-tyrosine. Both enantiomers of xylariamide A were tested in a brine shrimp lethality assay and only the natural product (1) showed toxicity.

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Journal of Natural Products

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68

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© 2005 American Chemical Society. Self-archiving of the author-manuscript version is not yet supported by this publisher.

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Chemical sciences

Biological sciences

Biomedical and clinical sciences

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