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Total synthesis of (+)-superstolide A

Academic Article
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Overview

authors

  • Tortosa, M.
  • Yakelis, N. A.
  • Roush, William

publication date

  • December 2008

journal

  • Journal of Organic Chemistry  Journal

abstract

  • A convergent and highly stereocontrolled total synthesis of the cytotoxic macrolide (+)-superstolide A is described. Key features of this synthesis include the use of bimetallic linchpin 36b for uniting the C(1)-C(15) (43) and the C(20)-C(27) (38) fragments of the natural product, a late-stage Suzuki macrocyclization of 49, and a highly diastereoselective transannular Diels-Alder reaction of macrocyclic octaene 4. In contrast, the intramolecular Diels-Alder reaction of pentaenal 5 provided the desired cycloadduct with lower stereoselectivity (6:1:1).

subject areas

  • Alcohols
  • Animals
  • Cyclization
  • Cytotoxins
  • Indicators and Reagents
  • Macrolides
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Porifera
  • Tetrahydronaphthalenes
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Identity

PubMed Central ID

  • PMC2736345

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo801794s

PubMed ID

  • 18956845
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Additional Document Info

start page

  • 9657

end page

  • 9667

volume

  • 73

issue

  • 24

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