105593-16-6Relevant articles and documents
Hydrolysis of Gibberellin 7-Methyl Esters: Anchimeric Assistance by a 15-Alcohol
Castellaro, Simon J.,MacMillan, Jake,Willis, Christine L.
, p. 2999 - 3004 (2007/10/02)
The neighbouring group effects of 15α- and 15β-hydroxy groups on the rate of hydrolysis of gibberellin 7-methyl esters are described.The presence of a 15-alcohol increases the rate of ester hydrolysis and a 15α- has a greater influence than a 15β-alcohol.The 15α-alcohol may be effective either through hydrogen bonding between the hydroxy proton and the ester carbonyl thus stabilising the tetrahedral intermediate formed on hydrolysis of the ester, or via 7,15α-lactonisation followed by hydrolysis of the lactone.The 15β-hydroxy may act through hydrogen bonding of a water molecule between the proton of the 15β-alcohol and the 7-carbonyl function.The effect is enhanced by the presence of a 13-acetate.