Enantioselective synthesis of protected forms of (3R,5R)-5- hydroxypiperazic acid useful for synthesis Journal Article
| Authors: | Depew, K. M.; Kamenecka, T. M.; Danishefsky, S. J. |
| Article Title: | Enantioselective synthesis of protected forms of (3R,5R)-5- hydroxypiperazic acid useful for synthesis |
| Abstract: | Protected versions of (3R,5R)-5-hydroxypiperazic acid were synthesized enantioselectively in two novel ways. The first derives its chirality from D- glutamic acid while the second uses an Evans amination and a diastereoselective bromolactonization to establish the two chiral centers. Given that this amino acid is a component of several depsipeptides, these two routes enable the synthesis of multigram quantities of protected versions of 2. |
| Keywords: | chemical structure; amination; piperazine derivative; reaction analysis; chemical reaction; synthesis; stereochemistry; depsipeptide; lactone derivative; chirality; enantiomer; annulation; bromine derivative; amino acid derivative; article; amino acid derivatives; lactonisation; dextro glutamic acid |
| Journal Title: | Tetrahedron Letters |
| Volume: | 41 |
| Issue: | 3 |
| ISSN: | 0040-4039 |
| Publisher: | Pergamon-Elsevier Science Ltd |
| Date Published: | 2000-01-15 |
| Start Page: | 289 |
| End Page: | 292 |
| Language: | English |
| DOI: | 10.1016/s0040-4039(99)01958-9 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 18 November 2015 -- Source: Scopus |
