Synthesis of the Antibiotic ( R )‐Reutericyclin  via Dieckmann  Condensation | Zendy

Böhme Roswitha | Zendy; Jung Günther | Zendy; Breitmaier Eberhard | Zendy

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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%.

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