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

Authors :: Chavan, Subhash P.
Harale, Kishor R.
Puranik, Vedavati G.
Gawade, Rupesh L.
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. May2012, Vol. 53 Issue 21, p2647-2650. 4p.
Publication Year :: 2012
Abstract: Abstract: 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. [Copyright &y& Elsevier]

Subjects :: *EPIMERIZATION
*PYROGLUTAMIC acid
*ALLYLATION
*METATHESIS reactions
*OXIDATION
*HETEROCYCLIC compounds synthesis

Language :: English
ISSN :: 00404039
Volume :: 53
Issue :: 21
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 74308036
Full Text :: https://doi.org/10.1016/j.tetlet.2012.03.054