Synthesis of ent-Haterumalide NA (ent-Oocydin A) Methyl Ester

Stille coupling of allylic chloride 26 with vinylstannane 4a afforded 65% of 27 with the requisite skipped diene, vinyl chloride, and allylic oxygen functionality. Yamaguchi macrolactonization of 28 provided 65% of 29, which was elaborated to haterumalide NA methyl ester (32) by a Nozaki−Hiyama−Kishi coupling with 31.