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

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Abstract

(Equation presented) 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.

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Gu, Y., & Snider, B. B. (2003). Synthesis of ent-Haterumalide NA (ent-Oocydin A) Methyl Ester. Organic Letters, 5(23), 4385–4388. https://doi.org/10.1021/ol0356789

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