## 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 e
Synthesis of the Antibiotic (R)-Reutericyclin via Dieckmann Condensation.
✍ Scribed by Roswitha Boehme; Guenther Jung; Eberhard Breitmaier
- Book ID
- 101981314
- Publisher
- John Wiley and Sons
- Year
- 2006
- Weight
- 15 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0931-7597
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📜 SIMILAR VOLUMES
## Abstract Starting from dimethyl‐L‐tartrate, the convenient two‐step sequence allows the preparation of enantiopure target compounds (IV) via double Dieckmann condensation of esters (III).
## Abstract Reaction of acyloxyesters containing a trifluoroethoxy group (I) and (III) with LiHMDS proceeds via tandem Dieckmann condensation—alkoxide β‐elimination to give pulvinones (II) and (IV), respectively.
~Ketoesters useful for elaboration to carbacephems were synthesized from a variety of enantiomerically pure diesters. Use of phenyl esters to direct the regioselectivity was demonstrated.