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

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

11 Citations (Scopus)

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
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
Publication status	Published - 2006

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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.\}",

year = "2006",

doi = "10.1039/b603570a",

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journal = "Organic and Biomolecular Chemistry",

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AU - Crow, James R.

AU - Thomson, Regan J.

AU - Mander, Lewis N.

PY - 2006

Y1 - 2006

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.

UR - https://www.scopus.com/pages/publications/33745454985

U2 - 10.1039/b603570a

DO - 10.1039/b603570a

M3 - Article

SN - 1477-0520

VL - 4

SP - 2532

EP - 2544

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 13

ER -

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

Abstract

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