Synthesis of the C1-C21 domain of azaspiracids-1 and -3

Org Lett. 2013 May 17;15(10):2338-41. doi: 10.1021/ol400487e. Epub 2013 Apr 29.

Abstract

An efficient synthesis of the C1-C21 fragment of azaspiracids-1 and -3 is described. This features a Nozaki-Hiyama-Kishi reaction to couple the AB and CD ring precursors and formation of the THF-fused ABCD trioxadispiroketal system under thermodynamic conditions.

Publication types

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

MeSH terms

  • Furans / chemical synthesis*
  • Furans / chemistry
  • Marine Toxins / chemical synthesis*
  • Marine Toxins / chemistry
  • Molecular Structure
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism
  • Thermodynamics

Substances

  • Furans
  • Marine Toxins
  • Pyrans
  • Spiro Compounds
  • azaspiracid
  • azaspiracid-2