Intramolecular reactions of compounds derived from sugars. Part III. High diastereoselection in the intramolecular diels-alder reaction of sugar based 1,7(E,Z),9-decatrienes

Pál Herczegh, Zsély Martina, Szilágyi László, Dinya Zoltán, Bognár Rezso

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

A mixture of tetrachiral deca-1, 7E, 9-triene 5 and its 7z isomer 6 was prepared from D-glucose by the use of two Wittig olefination reactions. When 5 or 6 were subjected to intramolecular Diels-Alder reaction under thermal conditions the same, cis-fused octahydronaphtalene enantiomer 9 was formed exclusively. This phenomenon can be explained by Z→E isomerization of 6 to 5. Similaryly, when a mixture of trienones 7 and 8 was heated at 160° the formation of a single product 10 was observed. Stereochemical outcome of the reactions can be rationalized by inspection of the possible conformers leading to transition states.

Original languageEnglish
Pages (from-to)5995-6002
Number of pages8
JournalTetrahedron
Volume45
Issue number18
DOIs
Publication statusPublished - 1989

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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