Synthesis of the C1-C19 Domain of Azaspiracid-34

Org Lett. 2019 Jan 18;21(2):356-359. doi: 10.1021/acs.orglett.8b03451. Epub 2019 Jan 2.

Abstract

Azaspiracid-34 (AZA34) is a recently described structurally unique member of the azaspiracid class of marine neurotoxins. Its novel structure, tentatively assigned on the basis of MS and 1H NMR spectroscopy, is accompanied by a 5.5-fold higher level of toxicity against Jurkat T lymphocytes than AZA1. To completely assign the structure of AZA34 and provide material for in-depth biological evaluation and detection, synthetic access to AZA34 was targeted. This began with the convergent and stereoselective assembly of the C1-C19 domain of AZA34 designed to dovetail with the recent total synthesis approach to AZA3.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Humans
  • Jurkat Cells / chemistry
  • Jurkat Cells / cytology*
  • Magnetic Resonance Spectroscopy
  • Marine Toxins / chemical synthesis
  • Marine Toxins / chemistry
  • Marine Toxins / toxicity*
  • Molecular Structure
  • Neurotoxins / toxicity*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry

Substances

  • Marine Toxins
  • Neurotoxins
  • Spiro Compounds
  • azaspiracid