A multicomponent coupling strategy suitable for the synthesis of the triene component of the oxazolomycin antibiotics

Paul G. Bulger, Mark G. Moloney, Paul C. Trippier

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Concise and versatile routes suitable for the synthesis of three geometric isomers of an analogue of the left hand triene sub-unit of oxazolomycin are reported. A strategy based upon a key Heck reaction was unsuccessful, and this was traced to a combination of steric encumbrance and electronic deactivation of the alkene substrate. An alternative Stille coupling strategy, however, proved to be both versatile and high yielding, and is potentially applicable to the synthesis of analogues with variation both in the side-chain geometry and in the identity of the terminal aromatic or heteroaromatic residue.

Original languageEnglish (US)
Pages (from-to)3726-3737
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume1
Issue number21
DOIs
StatePublished - Nov 7 2003

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trienes
antibiotics
Alkenes
Hand
analogs
Anti-Bacterial Agents
synthesis
Isomers
deactivation
alkenes
isomers
routes
Geometry
Substrates
geometry
electronics
diffusomycin

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

A multicomponent coupling strategy suitable for the synthesis of the triene component of the oxazolomycin antibiotics. / Bulger, Paul G.; Moloney, Mark G.; Trippier, Paul C.

In: Organic and Biomolecular Chemistry, Vol. 1, No. 21, 07.11.2003, p. 3726-3737.

Research output: Contribution to journalArticle

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