The stereochemistry of reduction of A gibberellin Δ1-unsaturated ketone
Abstract
Whilst sodium borodeuteride reduction of gibberellin A3 3-ketone which affords gibberellin A1, and its 3-epimer, proceeds stereospecifically from the β-face at C-1, the reaction has only limited stereoselectivity at C-2 affording in the case of 3-epi-gibberellin A1, methyl ester, a 2α: 2β-2H ratio of 0.35–0.5:1 thus revising a previous conclusion.