81826-97-3

Upstream product

• 83455-33-8 1-oxo-GA₂₀ 
• 81827-04-5 gibberellin A₆₀ methyl ester 
• 77-06-5 (3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid 
• 123592-77-8 C₂₅H₃₆O₈ 
• 123592-49-4 C₁₉H₂₄O₅ 
• 79216-98-1 1β-Azido-gibberellin A₁ 
• 82225-44-3 1-oxo-GA₁ 
• 83455-32-7 1-oxo-GA₅ 
• 5087-25-2 gibberellin A₃-ketone 
• 81827-02-3 ent-1α,13-diacetoxy-10-hydroxy-3β-thiobenzoyloxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone 
• 81826-95-1 C₂₇H₃₂N₂O₈S 
• 81827-03-4 ent-1α,13-diacetoxy-10-hydroxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone 
• 35316-73-5 ent-1α,13-dihydroxy-3-oxo-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone 
• 129082-46-8 C₂₅H₃₆O₉ 

Relevant academic research and scientific papers

GIBBERELLINS-LXXXIX. SYNTHESIS OF GIBBERELLIN A55 AND A57 AS WELL AS 1-OXYGENATED GIBBERELLIN A5 AND A20 ANALOGUES-A NEW PRINCIPLE FOR THE REGIOSELECTIVE TRANSPOSITION OF AN ALLYLIC ALCOHOL FUNCTION

The synthesis of a series of 1-oxygenated gibberellins starting from GA3 (1) is described.Nucleophilic addition of hydrazoic acid to 3-dehydro GA3 (2) was followed by NaBH4 reduction of the resulting 1-azido-3-ketones 4 and 5 to the corresponding azido alcohols 8-10, and photolysis of the latter compounds to instable 1-imines which were smoothly hydrolysed to the 1-oxo-3-hydroxy gibberellins 13 and 14.Subsequent NaBH4 reduction led to GA57 (19) and GA55 (20) and their 3-epimers, 17 and 18 respectively.In further steps 1-oxo-GA5 (21), 1α- and 1β-hydroxy-GA5 (23 and 24), 1-oxo-GA20 (25) as well as 1α- and 1β-hydroxy-GA20 (26 and 27) were available.The structures of the synthesized gibberellins were determined by physical data, in regard to the stereochemistry at C-1 and C-3 especially on the basis of 1H NMR and ORD measurements.

Gibberellins A60, A61, and A62: Partial Syntheses and Natural Occurrence

ent-1α,10,13-Trihydroxy-20-norgibberell-16-ene-7,19-dionic acid 19,10 lactone (gibberellin A60) and ent-1α,10-dihydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone (gibberellin A61) have been prepared from gibberellin A3 and gibberellin A7, respectively, and shown to be identical with two gibberellins previously detected by g.l.c.-mass spectrometry in developing grains of Triticum aestivum. ent-1α,10-Dihydroxy-20-norgibberella-2,16-diene-7,19-dioic acid 19,10-lactone (gibberellin A62) has also been prepared from gibberellin A7 and shown to be present in the grain of T. aestivum.Gibberellins A61 and A62 have also been detected in immature seed of Pyrus malus.Attempts to prepare a fourth putative gibberellin, detected in T. aestivum, were not successful.