Cyclohexane analogues of the antifungal icofungipen [(1R,2S)-2-amino-4-methylenecy
clopentanecarboxylic acid] were selectively synthesized from unsaturated bicyclic beta-lactams
by transformation of the ring olefinic bond through three different regio- and stereocontrolled
hydroxylation techniques, followed by hydroxy group oxidation and oxo-methylene
interconversion with a phosphorane. Starting from an enantiomerically pure bicyclic beta-lactam
obtained by enzymatic resolution of the racemic compound, an enantiodivergent procedure led to
the preparation of both dextro- and levorotatory cyclohexane analogues of icofungipen
