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Total synthesis of the depsipeptide FR-901375

Academic Article
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Overview

authors

  • Chen, Y. P.
  • Gambs, C.
  • Abe, Y.
  • Wentworth Jr., Paul
  • Janda, Kim

publication date

  • November 2003

journal

  • Journal of Organic Chemistry  Journal

abstract

  • The first total synthesis of FR-901375, a novel bicyclic depsipeptide isolated from the fermentation broth of Pseudomonas chloroaphis No. 2522, has been achieved. The synthetic approach involves 13 reaction steps and is achieved in 12% overall yield. The key points in the successful synthetic strategy are a concise asymmetric synthesis of the key building block (3R,4E)-3-hydroxy-7-mercapto-4-heptenoic acid, a mild Mitsunobu macrolactonization step, and an I(2)-mediated deprotection with concomitant disulfide-bridge formation.

subject areas

  • Depsipeptides
  • Peptides, Cyclic
  • Pseudomonas
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo034765b

PubMed ID

  • 14604360
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Additional Document Info

start page

  • 8902

end page

  • 8905

volume

  • 68

issue

  • 23

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