Synthesis of β-Resorcylic Macrolides via Organopalladium Chemistry. Application to the Total Synthesis of (S)-Zearalenone

Article abstract of DOI:10.1021/jo00008a053

The β-resorcyclic macrolides are a class of naturally occurring 12- and 14-membered macrolides.Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest.In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct β-resorcylic macrolides.The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones.This methodology was then used to prepare (S)-zearalenone (1).