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Enantioselective synthesis of heliannuol E; structural consideration of natural molecule

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
44
Issue
26
Identifiers
DOI: 10.1016/s0040-4039(03)01094-3
Keywords
  • Heliannuol E
  • Helianthus Annuusl. Cv. Sh-222
  • Allelopathy
  • Phenolic Oxidation
  • Ring Expansion
  • Spirodienone

Abstract

Abstract Heliannuol E 1 , isolated from Helianthus annuus L. cv. SH-222, was successfully synthesized in both optically active forms, by novel ring-expansion reaction of the corresponding spirodienone derivatives 8 and 17 , which were produced from 7 and 16 under anodic oxidation conditions. The absolute structure of the natural product was determined to have R-configuration at the benzylic position.

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