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Synthesis of the ABCDEFG ring system of maitotoxin

Academic Article
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Overview

related to degree

  • Aversa, Robert, Ph.D. in Synthetic Chemistry, Scripps Research 2006 - 2011

authors

  • Nicolaou, K.C.
  • Aversa, Robert
  • Jin, J.
  • Rivas, F.

publication date

  • 2010

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Maitotoxin (1) continues to fascinate scientists not only because of its size and potent neurotoxicity but also due to its molecular architecture. To provide further support for its structure and facilitate fragment-based biological studies, we developed an efficient chemical synthesis of the ABCDEFG segment 3 of maitotoxin. (13)C NMR chemical shift comparisons of synthetic 3 with the corresponding values for the same carbons of maitotoxin revealed a close match, providing compelling evidence for the correctness of the originally assigned structure to this polycyclic system of the natural product. The synthetic strategy for the synthesis of 3 relied heavily on our previously developed furan-based technology involving sequential Noyori asymmetric reduction and Achmatowicz rearrangement for the construction of the required tetrahydropyran building blocks, and employed a B-alkyl Suzuki coupling and a Horner-Wadsworth-Emmons olefination to accomplish their assembly and elaboration to the final target molecule.

subject areas

  • Furans
  • Magnetic Resonance Spectroscopy
  • Marine Toxins
  • Oxocins
  • Polycyclic Compounds
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Identity

PubMed Central ID

  • PMC2880607

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja102260q

PubMed ID

  • 20415445
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Additional Document Info

start page

  • 6855

end page

  • 6861

volume

  • 132

issue

  • 19

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