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Synthesis of the Antibiotic ( R )‐Reutericyclin via Dieckmann Condensation
Author(s) -
Böhme Roswitha,
Jung Günther,
Breitmaier Eberhard
Publication year - 2005
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200590226
Subject(s) - chemistry , moiety , derivative (finance) , yield (engineering) , enantiomer , stereochemistry , natural product , total synthesis , chloride , acetyl chloride , organic chemistry , medicinal chemistry , catalysis , materials science , financial economics , economics , metallurgy
( 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%.