Several approaches to the synthesis of a natural acetyl cholinesterase (AChE) inhibitor, cyclophostin and an isosteric endophosphonate analog were explored. These bicyclic molecules posses a novel seven membered cyclic enolphosphate/phosphonate ring fused to a butyrolactone. Two basic synthetic strategies: a) lactonization followed by the seven membered ring formation and b) the seven membered ring synthesis followed by lactonization, were applied in these syntheses. The synthesis of the endophosphonate analog, following strategy a, gave an unexpected enolether lactone molecule. ...
Several approaches to the synthesis of a natural acetyl cholinesterase (AChE) inhibitor, cyclophostin and an isosteric endophosphonate analog were exp...