Rearrangement of the lactone ring of gibberellin A3 in aqueous alkali; participation of the ionised 3-hydroxy-group in an anti S N2? reaction
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2117-2121
- https://doi.org/10.1039/p19800002117
Abstract
Whereas gibberellin A3 is completely rearranged by 0.01 M-aqueous sodium hydroxide at 22 °C to the 19,2-lactone, the methyl ethers of both reactant and product, the 3-epimer (as its 13-acetate), and 3-deoxygibberellin A3 methyl ester are all inert to aqueous base. A 2β,3β-epoxy-19-carboxylate intermediate in the rearrangement is proposed.This publication has 0 references indexed in Scilit: