Studies on the stereoselective selenolactonization, hydroxy and methoxy selenenylation of a- and b-hydroxy acids and esters. Synthesis of delta and gamma lactones

Michelangelo Gruttadauria, Paolo Maria Giuseppe Lo Meo, Francesca D'Anna, Renato Noto, Serena Riela, Maria E. Amato, Paolo Lo Meo, Paolo Lo Meo, Paolo Lo Meo, Serena Riela, Michelangelo Gruttadauria, Francesca D'Anna, Renato Noto, Carmela Aprile, Carmela Aprile

Risultato della ricerca: Articlepeer review

43 Citazioni (Scopus)

Abstract

The diastereoselective synthesis of hydroxy substituted γ- and δ-lactones was accomplished following two approaches. A 5- or 6-endo cyclization promoted by electrophilic selenium reagents of α- or β-hydroxy acids and a 5- or 6-exo cyclization of hydroxy esters obtained through a diastereoselective hydroxy selenenylation reaction of α- or β-hydroxy esters. Moreover, the diastereoselective methoxy selenenylation of the above compounds was investigated showing a case in which the compound that was unreactive in the hydroxy selenenylation conditions gave, in the methoxy selenenylation conditions, the deprotected diol. The usefulness of the methoxy selenenylation procedure was proven by the preparation of a symmetric compound unsymmetrically functionalized. Yields and selectivities were found to depend on substituents (Ph or alkyl groups at the carbon atom that undergoes the nucleophilic attack), mode of cyclization, kinetic or thermodynamic control conditions. In the latter case, silica gel played an important role.
Lingua originaleEnglish
pagine (da-a)2241-2251
Numero di pagine11
RivistaTetrahedron
Stato di pubblicazionePublished - 2003

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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