Synthesis and bioactivity of the gibberellin, 18 hydroxy-GA 1 (GA 132 )

Date

2008

Authors

Morrison (previously Beck), Ellen
Chandler, Peter
Thomson, Regan
Mander, Lewis

Journal Title

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Volume Title

Publisher

Royal Society of Chemistry

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.

Description

Keywords

Keywords: Amylase induction; Barley; Gibberellin; Intramolecular aldol reaction; Bioactivity; Biosynthesis; Hydroxylation; Molecular structure; Reaction kinetics; Hormones; 18 hydroxygibberellic acid 1; 18-hydroxygibberellic acid 1; amylase; gibberellic acid; gibbe

Citation

Source

Organic and Biomolecular Chemistry

Type

Journal article

Book Title

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DOI

10.1039/b800728d

Restricted until

2037-12-31