Formal synthesis of (−)-stemoamide using a useful epimerization at C-8

Formal synthesis of (−)-stemoamide using a useful epimerization at C-8

The formal synthesis of (−)-stemoamide was achieved starting from l-pyroglutamic acid. The key steps used are the allylation using BF3·OEt2, ring closing metathesis, allylic oxidation and a novel epimerization at C8.

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Veröffentlicht in:Tetrahedron letters 2012-05, Vol.53 (21), p.2647-2650
Hauptverfasser: Chavan, Subhash P., Harale, Kishor R., Puranik, Vedavati G., Gawade, Rupesh L.
Format: Artikel
Sprache:eng
Schlagworte:
Allyl compounds
Allylation
Allylic oxidation
Chemical reactions
Decomposition reactions
Metathesis
Oxidation
Pyroglutamic acid
Ring closing metathesis
Stemoamide
Synthesis (chemistry)
Tetrahedrons
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Zusammenfassung:The formal synthesis of (−)-stemoamide was achieved starting from l-pyroglutamic acid. The key steps used are the allylation using BF3·OEt2, ring closing metathesis, allylic oxidation and a novel epimerization at C8.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.03.054