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The structures of 9-hydroxyzinnolides and their rearranged acetates

Authors
Journal
Phytochemistry
0031-9422
Publisher
Elsevier
Publication Date
Volume
24
Issue
5
Identifiers
DOI: 10.1016/s0031-9422(00)83168-4
Keywords
  • Zinnia Acerosa
  • Z. Juniperifolia
  • Z. Peruviana
  • Compositae
  • Elemanolides
  • 9β-Hydroxyzinnolides
  • δ-Lactones
  • Juniperin
  • 11
  • 13-Dehydrozinarosin.
Disciplines
  • Chemistry

Abstract

Abstract Eleman-8β,12-olides containing a β-hydroxyl group at C-9 exist in equilibrium with 8β-hydroxyeleman-9,12-olides. Acetylation of 9β-hydroxyelemanolides gave a mixture of 8β-and 9β-acetyl derivatives in which the former predominates. The structures of zinaflorin II acetate, zinaflorin III and other 9β-hydroxyelemanolide acetates have been revised. The absolute stereochemistry of the δ-lactone juniperin has been established by means of an X-ray crystallographic analysis.

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