75884-81-0Relevant academic research and scientific papers
Substitution Reactions of the 3-Epimeric Methanesulphonates of Methyl Gibberellate
Duri, Zvitendo J.,Hanson, James R.
, p. 603 - 607 (2007/10/02)
Whereas displacement of the 3β-(axial)-methylsulphonyloxy group from methyl gibberellate with lithium chloride or buffered aqueous acetone proceeds predominantly with syn rearrangement to afford the 1β-chloro- or 1β-hydroxy-gibberellin, the corresponding 3α-(equatorial) epimer reacts with simple inversion of configuration.This affords on the one hand a facile route to the 1-hydroxygibberellins and, on the other, a means of labelling gibberellins at C-3.
Mechanism and Stereochemistry of Conjugate Reduction of Enones from Gibberellins A3 and A7
Beale, Michael H.,MacMillan, Jake
, p. 877 - 884 (2007/10/02)
Conjugate reduction of the methyl esters of 3-didehydrogibberellin A3 13-acetate and of 3-didehydrogibberellin A7, in aprotic solvents by borohydride (or borodeuteride), is shown to introduce hydrogen (or deuterium) at the 1β- and 3β-positions in the products, 3-epi-gibberellin A1 13-acetate and 3-epi-gibberellin A4 methyl esters.The third hydrogen (or deuterium) comes from the proton (or deuteron) source used in the work-up.A mechanism for conjugate reduction of enones is proposed.The products from the borodeuteride reduction of 3-didehydrogibberellin A7 methyl ester with proton and deuteron work-up were chemically converted into -, -, and -gibberellin A4 and the stereochemistries of the deuterium atoms were determined from the deuterium content of the metabolites, formed from these labelled gibberellins in cultures of Gibberella fujikuroi, mutant B1-41a.
