The synthesis of pentacyclic steroidal polyesters in consecutive Heck- and Diels-Alder reactions

György Jeges, Rita Skoda-Földes, László Kollár, Judit Horváth, Zoltán Tuba

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15 Citations (Scopus)

Abstract

Steroidal alkenyl iodides (17-iodo-androsta-16-ene and 17-iodo-4- methyl-4-aza-androsta-16-ene-3-one) were reacted with conjugated unsaturated esters (ethyl acrylate, diethyl fumarate, diethyl maleate, diethyl acetylene dicarboxylate) in Heck-reaction and consecutive Diels-Alder reaction resulting in facile formation of pentacyclic derivatives. All steroidal esters possessing two, three and four ester functionalities on the E-ring were formed by the α-side addition of the dienophile.

Original languageEnglish
Pages (from-to)6767-6780
Number of pages14
JournalTetrahedron
Volume54
Issue number24
DOIs
Publication statusPublished - Jun 11 1998

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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