Synthesis of ent-haterumalide NA (ent-oocydin A) methyl ester.
[reaction: see text] 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.
Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Yonghong
Y
Gu
Barry B
BB
Snider
D004952:Esters; D018942:Macrolides / Q000138:chemical synthesis*
D004952:Esters; D018942:Macrolides