Abstract
Abstract(R)‐Reutericyclin ((R)‐1), a bactericidal, amphiphilic natural product with a trisubstituted tetramic acid moiety, was prepared in four steps from D‐leucine in an overall yield of 24%. The chiral heterocyclic portion of 1 was synthesized by Dieckmann cyclization of ethyl N‐(acetoacetyl)leucinate (7), and the resulting pyrrole derivative 8 was N‐acylated with (E)‐dec‐2‐enoyl chloride in the presence of BuLi at − 70° (Scheme 2). This new procedure is straightforward and allows the synthesis of both antipodes of reutericyclin in an enantiomeric excess (ee) of ca. 80%.
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