Stereoselective Synthesis of the Epicoccin Core

Stereoselective Synthesis of the Epicoccin Core

A short, convergent, and asymmetric synthesis of the epicoccin core was achieved using a phosphite-promoted one-step condensation of a complex proline-type amino acid. Key features of the assembly of this amino acid were a double-bond isomerization/vinylation/ring-closing metathesis strategy as well...

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Veröffentlicht in:Organic letters 2009-10, Vol.11 (20), p.4740-4742
Hauptverfasser: Gross, Ulrike, Nieger, Martin, Bräse, Stefan
Format: Artikel
Sprache:eng
Schlagworte:
Cyclohexenes - chemistry
Isomerism
Lactones - chemistry
Piperazines - chemistry
Stereoisomerism
Substrate Specificity
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Beschreibung
Zusammenfassung:A short, convergent, and asymmetric synthesis of the epicoccin core was achieved using a phosphite-promoted one-step condensation of a complex proline-type amino acid. Key features of the assembly of this amino acid were a double-bond isomerization/vinylation/ring-closing metathesis strategy as well as an efficient, highly diastereoselective [2 + 2] cycloaddition of a ketene to an enecarbamate, derived from l-pyroglutamic acid.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol901919c