Alkene protection against acid using a bromide substituent: Application in a total synthesis of (-)-6,7-dideoxysqualestatin H5

Hasanain A.A. Almohseni, Hamad Al Mamari, Anne Valade, Herman O. Sintim, David M. Hodgson

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The presence of a bromide substituent, instead of a hydrogen or methyl group, on a carbon-carbon double bond, protects the alkene from addition reactions when exposed to trifluoroacetic acid. This concept is used to circumvent concomitant loss of unsaturation in a late-stage acid-catalysed 6,8- to 2,8-dioxabicyclo[3.2.1]octane rearrangement towards (-)-6,7-dideoxysqualestatin H5. The inertness of the alkenyl bromide functionality is demonstrated through several synthetic transformations in the assembly of the rearrangement substrate. Completion of the natural product synthesis is facilitated by post-rearrangement removal of the bromide substituent through stereoselective C-C cross-coupling in the presence of ester and hydroxyl functionalities.

Original languageEnglish
Pages (from-to)5354-5356
Number of pages3
JournalChemical Communications
Volume54
Issue number42
DOIs
Publication statusPublished - Jan 1 2018

Fingerprint

Alkenes
Bromides
Olefins
Trifluoroacetic acid
Addition reactions
Carbon
Acids
Trifluoroacetic Acid
Esters
Biological Products
Hydroxyl Radical
Hydrogen
Substrates
6,7-dideoxysqualestatin H5

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

Alkene protection against acid using a bromide substituent : Application in a total synthesis of (-)-6,7-dideoxysqualestatin H5. / Almohseni, Hasanain A.A.; Al Mamari, Hamad; Valade, Anne; Sintim, Herman O.; Hodgson, David M.

In: Chemical Communications, Vol. 54, No. 42, 01.01.2018, p. 5354-5356.

Research output: Contribution to journalArticle

Almohseni, Hasanain A.A. ; Al Mamari, Hamad ; Valade, Anne ; Sintim, Herman O. ; Hodgson, David M. / Alkene protection against acid using a bromide substituent : Application in a total synthesis of (-)-6,7-dideoxysqualestatin H5. In: Chemical Communications. 2018 ; Vol. 54, No. 42. pp. 5354-5356.
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