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

TitleFormal synthesis of (-)-stemoamide using a useful epimerization at C-8
Publication TypeJournal Article
Year of Publication2012
AuthorsChavan, SP, Harale, KR, Puranik, VG, Gawade, RL
JournalTetrahedron Letters
Volume53
Issue21
Pagination2647-2650
Date PublishedMAY
ISSN0040-4039
KeywordsAllylation, Allylic oxidation, Pyroglutamic acid, Ring closing metathesis, Stemoamide
Abstract

The formal synthesis of (-)-stemoamide was achieved starting from L-pyroglutamic acid. The key steps used are the allylation using BF3 center dot OEt2, ring closing metathesis, allylic oxidation and a novel epimerization at C8. (C) 2012 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2012.03.054
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.397

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry