Convenient preparation of (Z)-α-halo-α,β-unsaturated aldehydes: synthesis of a Laurencia flexilis toxin

Deb K. Barma, Biao Lu, Rachid Baati, Charles Mioskowski, J R Falck

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

The CrCl2-mediated two-carbon halo-homologation of aryl, alkenyl, and aliphatic aldehydes with chloral ethyl hemiacetal or bromal affords (Z)-α-chloro- and (Z)-α-bromo-α,β-unsaturated aldehydes, respectively, in good to excellent yields and high stereoselectivity. The utility of this methodology was illustrated by a synthesis of 2-chloropentadec-2(Z)-enal, a toxin isolated from the marine red alga Laurencia flexilis.

Original languageEnglish (US)
Pages (from-to)4359-4361
Number of pages3
JournalTetrahedron Letters
Volume49
Issue number28
DOIs
StatePublished - Jul 7 2008

Keywords

  • Aldehydes
  • Chromium
  • Enals
  • Homologation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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