Liu, JinMander, LewisKoshioka, Masaji2015-12-132015-12-131551-7004http://hdl.handle.net/1885/77887A general procedure has been established for the synthesis of 11,13-dihydroxy gibberellins. The key steps involve the isomerization of the 19,10 lactone functionality to the 19,2-isomer, bromination at C-1 and C-11, then selective nucleophilic displacement of the 11-bromo substituent by acetate with silver(1) acetate. Reconstitution of the 19,10 lactone functionality was effected by bromolactonization of a Δ9-ene 19-carboxylic acid to give a 9β-bromo 19,10-lactone followed by stereoselective hydrogenolysis of the bromo substituent.Keywords: acetic acid; carboxylic acid derivative; gibberellin derivative; lactone derivative; silver derivative; article; bromination; hydrogenolysis; isomer; isomerization; methodology; stereochemistry; synthesis 11-Hydroxy-gibberellins; Bromo-lactonization; Loquat; Nucleophilic substitution; Silver ion20042015-12-11