Stereoselective iodolactonization of acyclic unsaturated 3-hydroxyacids

A. Richard Chamberlin, Milana Dezube, Patrick H Dussault

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

A stereoselective method for preparing 3-hydroxy-4-alkyl-γ-lactones is reported. iodolactonization of 3-hydroxy-4-alkenoic acids produces predominantly the thermodynamically less stable 3,4-cis products, which undergo methanolysis to threo-epoxyalcohols.

Original languageEnglish (US)
Pages (from-to)4611-4614
Number of pages4
JournalTetrahedron Letters
Volume22
Issue number46
DOIs
StatePublished - Jan 1 1981
Externally publishedYes

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Lactones
Carboxylic acids
Acids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Stereoselective iodolactonization of acyclic unsaturated 3-hydroxyacids. / Chamberlin, A. Richard; Dezube, Milana; Dussault, Patrick H.

In: Tetrahedron Letters, Vol. 22, No. 46, 01.01.1981, p. 4611-4614.

Research output: Contribution to journalArticle

Chamberlin, A. Richard ; Dezube, Milana ; Dussault, Patrick H. / Stereoselective iodolactonization of acyclic unsaturated 3-hydroxyacids. In: Tetrahedron Letters. 1981 ; Vol. 22, No. 46. pp. 4611-4614.
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