Stereostructure of a Novel Cytotoxic 18-Membered Macrolactone Antibiotic FD-891

The absolute stereochemistry of FD-891, a novel cytotoxic 18-membered macrolactone antibiotic, was determined by a synthetic approach as well as X-ray diffraction of degradative derivatives. The absolute configuration of FD-891 turned out to be as shown above. The stable conformer of FD-891 was also...

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Bibliographic Details
Published in:	Organic letters Vol. 4; no. 20; pp. 3383 - 3386
Main Authors:	Eguchi, Tadashi, Kobayashi, Kayako, Uekusa, Hidehiro, Ohashi, Yuji, Mizoue, Kazutoshi, Matsushima, Yoshitaka, Kakinuma, Katsumi
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 03-10-2002
Subjects:	Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - toxicity Macrolides Magnetic Resonance Spectroscopy Molecular Conformation Molecular Structure Stereoisomerism X-Ray Diffraction
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Summary:	The absolute stereochemistry of FD-891, a novel cytotoxic 18-membered macrolactone antibiotic, was determined by a synthetic approach as well as X-ray diffraction of degradative derivatives. The absolute configuration of FD-891 turned out to be as shown above. The stable conformer of FD-891 was also discussed with respect to biological activity by comparison with the structurally related concanamycin A on the bases of molecular mechanics calculations.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol026518k