An expedient synthesis of the amide analog of the potent antifungal lipopeptidolactone FR901469

An expedient synthesis of the lactam analog ( 2 ) of the 40-membered lipopeptidolactone antifungal antibiotic, FR901469 ( 1 ), is described. The key steps in this synthesis are a novel biotransformation of the natural product to produce the highly versatile linear peptide building block 3 , and effi...

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Bibliographic Details
Published in:Tetrahedron letters 2001-01, Vol.42 (4), p.703-705
Main Authors: Barrett, David, Tanaka, Akira, Fujie, Akihiko, Shigematsu, Nobuharu, Hashimoto, Michizane, Hashimoto, Seiji
Format: Article
Language:English
Subjects:
antifungals
macrocycles
microbial reactions
peptides and polypeptides
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Summary:An expedient synthesis of the lactam analog ( 2 ) of the 40-membered lipopeptidolactone antifungal antibiotic, FR901469 ( 1 ), is described. The key steps in this synthesis are a novel biotransformation of the natural product to produce the highly versatile linear peptide building block 3 , and efficient formation of the 40-membered ring by macrolactamization under high-dilution conditions. Novel methology to prepare 2 from the natural product 1 is described.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)02047-5