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Synthesis of the Antibiotic (R)-Reutericyclin via Dieckmann Condensation

✍ Scribed by Roswitha Böhme; Günther Jung; Eberhard Breitmaier

Book ID
102261081
Publisher
John Wiley and Sons
Year
2005
Tongue
German
Weight
79 KB
Volume
88
Category
Article
ISSN
0018-019X

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✦ Synopsis

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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