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Total synthesis of (±)-nisamycin

Wipf, P and Coish, PDG (1999) Total synthesis of (±)-nisamycin. Journal of Organic Chemistry, 64 (14). 5053 - 5061. ISSN 0022-3263

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We have developed a highly convergent synthesis of the manumycin-type m- C7N-antibiotic nisamycin that is applicable to other members of this family of antibiotics. The synthesis features a three-step sequence to the epoxyquinol core that serves as a scaffold for the attachment of the polyene side chains. The eastern polyene side chain was constructed via a novel organozirconocene-mediated synthesis. Zirconocene methodology was also applied to the synthesis of the polyene side chains of asukamycin. The southern side chain of nisamycin was introduced via a Stille reaction that employed a vinyl bromo ketone, derived from an acid-sensitive bromo ketal. Pd-mediated coupling of the vinyl bromide with a stannyl TIPS ester gave TIPS-protected nisamycin that was readily converted to the natural product.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Coish, PDG
Date: 9 July 1999
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 64
Number: 14
Page Range: 5053 - 5061
DOI or Unique Handle: 10.1021/jo990413m
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
Date Deposited: 22 Jul 2015 13:52
Last Modified: 22 Jun 2021 12:55


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