Synthesis and confirmation of structure for the gibberellin GA 131 (18-hydroxy-GA4)

James R. Crow; Regan J. Thomson; Lewis N. Mander

doi:10.1039/b603570a

Synthesis and confirmation of structure for the gibberellin GA ₁₃₁ (18-hydroxy-GA₄)

James R. Crow, Regan J. Thomson, Lewis N. Mander^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

A general method for the hydroxylation of the 18-methyl group in gibberellins has been developed, as demonstrated by the successful synthesis of 18-hydroxy GA₄ (GA₁₃₁) by means of a tandem process involving the conjugate addition of alkoxides to the α-methylene lactone moiety of a ring A-seco-gibberellin followed by an intramolecular aldol reaction.

Original language	English (US)
Pages (from-to)	2532-2544
Number of pages	13
Journal	Organic and Biomolecular Chemistry
Volume	4
Issue number	13
DOIs	https://doi.org/10.1039/b603570a
State	Published - 2006

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis and confirmation of structure for the gibberellin GA 131 (18-hydroxy-GA4)",

abstract = "A general method for the hydroxylation of the 18-methyl group in gibberellins has been developed, as demonstrated by the successful synthesis of 18-hydroxy GA4 (GA131) by means of a tandem process involving the conjugate addition of alkoxides to the α-methylene lactone moiety of a ring A-seco-gibberellin followed by an intramolecular aldol reaction.",

author = "Crow, {James R.} and Thomson, {Regan J.} and Mander, {Lewis N.}",

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doi = "10.1039/b603570a",

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AU - Thomson, Regan J.

AU - Mander, Lewis N.

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N2 - A general method for the hydroxylation of the 18-methyl group in gibberellins has been developed, as demonstrated by the successful synthesis of 18-hydroxy GA4 (GA131) by means of a tandem process involving the conjugate addition of alkoxides to the α-methylene lactone moiety of a ring A-seco-gibberellin followed by an intramolecular aldol reaction.

AB - A general method for the hydroxylation of the 18-methyl group in gibberellins has been developed, as demonstrated by the successful synthesis of 18-hydroxy GA4 (GA131) by means of a tandem process involving the conjugate addition of alkoxides to the α-methylene lactone moiety of a ring A-seco-gibberellin followed by an intramolecular aldol reaction.

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ER -

Synthesis and confirmation of structure for the gibberellin GA ₁₃₁ (18-hydroxy-GA₄)

Abstract

ASJC Scopus subject areas

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