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Total synthesis of (+)-13-deoxytedanolide

Academic Article
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Overview

authors

  • Julian, L. D.
  • Newcom, J. S.
  • Roush, William

publication date

  • May 2005

journal

  • Journal of the American Chemical Society  Journal

abstract

  • A total synthesis of 13-deoxytedanolide is described. The synthesis features a highly stereoselective fragment assembly aldol reaction of methyl ketone 4 and aldehyde 5 to establish the complete carbon skeleton of the natural product in the form of aldol 15. The facile formation of the remarkably unreactive hemiketal 16 thwarted attempts to elaborate 15 to tedanolide. However, deoxygenation of the C(13)-hydroxyl of 16 provided the 13-deoxy hemiketal 17 that was smoothly elaborated to 13-deoxytedanolide.

subject areas

  • Animals
  • Macrolides
  • Porifera
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja050729d

PubMed ID

  • 15853320
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Additional Document Info

start page

  • 6186

end page

  • 6187

volume

  • 127

issue

  • 17

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