General strategy for a short and efficient synthesis of 3-hydroxy-4-methylprolines (HMP)

TitleGeneral strategy for a short and efficient synthesis of 3-hydroxy-4-methylprolines (HMP)
Publication TypeJournal Article
Year of Publication2006
AuthorsMohapatra, DK, Mondal, D, Chorghade, MS, Gurjar, MK
JournalTetrahedron Letters
Volume47
Issue52
Pagination9215-9219
Date PublishedDEC
Type of ArticleArticle
ISSN0040-4039
Keywords3, 4-disubstituted proline, Crimmins' aldol reaction, Garner's aldehyde, non-proteinogenic amino acids, RUO4 mediated oxidation
Abstract

The non-proteinogenic amino acid 3-hydroxy-4-methylproline (HMP) is an active constituent of some potent antimicrobials including echinocandins, nostopeptins, pneumocandins, sporiofungin and mulundocandins. A synthesis has been achieved in 10 steps with 29% overall yield; the Evans' aldol reaction using Crimmins' modified method was pivotal to the success of the strategy. (c) 2006 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2006.10.137
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)2.645
Divison category: 
Organic Chemistry