22553-18-0

Upstream product

• 2074-31-9 3-didehydroGA₇ 
• 2619-66-1 3-didehydroGA₄ 
• 77584-35-1 +/-gibberellin A₄ 3-benzoate 
• 77584-34-0 C₂₆H₂₈O₇ 
• 2348-07-4 C₁₉H₂₄O₆ 

Downstream Products

• 2074-29-5 gibberellin A₄ methyl ester 
• 79368-09-5 GA₄ phenacyl ester 
• 79368-10-8 3-epiGA₄ phenacyl ester 
• 79368-20-0 benzoylmethyl ent-10β-hydroxy-17,20-bisnor-16-oxo-3α-toluene-p-sulphonyloxygibberellan-7-oate-19-oic acid 
• 79368-19-7 GA₄ norketone phenacyl ester 
• 79368-21-1 2,3-didehydroGA₉ norketone phenacyl ester 

Relevant academic research and scientific papers

STEREOSELECTIVE REDUCTION OF 3-KETO GIBBERELLIN ACIDS TO 3β-OLS USING K-SELECTRIDE WITH KH2PO4 BUFFER

KH2PO4 buffered K-Selectride gives with 3-keto gibberellin acids, borates which are reduced stereoselectively to 3β-ols.

Probing the mechanism of loss of carbon-20 in gibberellin biosynthesis. Synthesis of gibberellin 3α,20-hemiacetal and 19,20-lactol analogues and their metabolism by a recombinant GA 20-oxidase

A gibberellin 3α,20-hemiacetal,1 (equivalent to 3-epi-gibberellin A36), has been synthesised from gibberellin A13. Turnover of this hemiacetal by recombinant gibberellin 20-oxidase occurred with loss of the 20-carbon atom to give the 20-nor-19,10-lactone (3-epi-gibberellin A4). In addition, two other enzyme products were detected and identified by synthesis as 3-epi-20-norgibberellin A13 and 3-epi-1,10-didehydro-20-norgibberellin A13. These by-products indicate that the enzymatic reaction proceeds via a C-10 radical intermediate. Carbon radicals at C-10 and acyl radicals at C-20 were generated chemically and their decomposition products were studied with reference to the biological mechanism. The corresponding 19-nor-3α,20-hemiacetal 3 and 19-methylene analogue 4 were synthesised but were not oxidised at C-20 by the enzyme. These results indicate that the 19-carboxylic acid is an essential component of the enzyme reaction.

PREPARATION OF 2- AND 3-SUBSTITUTED GIBBERELLINS A9 AND A4 FOR BIOASSAY

Key Word Index - Partial synthesis; 2α,2β- and 3β-derivatives; gibberellin A4; gibberellin A9. To test the effects of preventing enzymatic 2β- and 3β-hydroxylation on the biological activities of gibberellins, the preparation of the following compounds is described: 2β-methyl- and 2,2-dimethyl-gibberellins A4 and A9; 2α-fluoro-, 2β-fluoro- and 2β-methoxy-gibberellin A9; and 3β-fluoro, 3β-methoxy-and 3-methylene A9.

TOTAL SYNTHESIS OF GIBBERELLIN A4

A general approach to the preparation of 13-deoxy C19 gibberellins has been established with the total synthesis of (+/-)gibberellin A4 (3).