Synthesis and bioactivity of the gibberellin, 18-hydroxy-GA1 (GA132)

Ellen Morrison, Peter M. Chandler, Regan J. Thomson, Lewis N. Mander

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

As part of a study to confirm putative structural assignments to new gibberellins and to furnish sufficient quantities for biological investigations, a twenty step synthesis of 18-hydroxy GA1 from gibberellic acid (GA3) is described, allowing the confirmation of structure for a new gibberellin, GA132, that occurs in developing grains of barley (Hordeum vulgare). The early part of the sequence involved cleavage of the C(3)-C(4) bond in the A-ring of a 3-oxo intermediate. The ring was then reformed as part of a "domino" process involving the conjugate addition of alkoxide to an α-methylene lactone moiety followed by an intramolecular aldol reaction. The bioactivities of the new GA, and its 18-hydroxy-GA 4 relative, have been confirmed in dwarf barley growth and α-amylase induction assays.

Original languageEnglish (US)
Pages (from-to)1416-1424
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume6
Issue number8
DOIs
StatePublished - 2008

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis and bioactivity of the gibberellin, 18-hydroxy-GA<sub>1</sub> (GA<sub>132</sub>)'. Together they form a unique fingerprint.

Cite this