| dc.contributor.author |
Koulocheri, SD |
en |
| dc.contributor.author |
Magiatis, P |
en |
| dc.contributor.author |
Skaltsounis, A-L |
en |
| dc.contributor.author |
Haroutounian, SA |
en |
| dc.date.accessioned |
2014-06-06T06:44:59Z |
|
| dc.date.available |
2014-06-06T06:44:59Z |
|
| dc.date.issued |
2002 |
en |
| dc.identifier.issn |
00404020 |
en |
| dc.identifier.uri |
http://dx.doi.org/10.1016/S0040-4020(02)00674-9 |
en |
| dc.identifier.uri |
http://62.217.125.90/xmlui/handle/123456789/2194 |
|
| dc.subject |
δ-lactam |
en |
| dc.subject |
2-pyridone |
en |
| dc.subject |
Pipecolic acid |
en |
| dc.subject.other |
3 hydroxypipecolic acid |
en |
| dc.subject.other |
amide |
en |
| dc.subject.other |
azide |
en |
| dc.subject.other |
lactam derivative |
en |
| dc.subject.other |
pipecolic acid derivative |
en |
| dc.subject.other |
pyridone derivative |
en |
| dc.subject.other |
unclassified drug |
en |
| dc.subject.other |
article |
en |
| dc.subject.other |
chirality |
en |
| dc.subject.other |
diastereoisomer |
en |
| dc.subject.other |
drug synthesis |
en |
| dc.subject.other |
hydroxylation |
en |
| dc.subject.other |
oxidation |
en |
| dc.subject.other |
priority journal |
en |
| dc.subject.other |
stereochemistry |
en |
| dc.title |
Asymmetric synthesis of (2R,3S)-3-hydroxypipecolic acid δ-lactam derivatives |
en |
| heal.type |
journalArticle |
en |
| heal.identifier.primary |
10.1016/S0040-4020(02)00674-9 |
en |
| heal.publicationDate |
2002 |
en |
| heal.abstract |
A practical synthetic scheme that incorporates an amide functionality into the rigid framework of (2S,3R)-3-hydroxypipecolic acid to produce novel hydroxylated δ-lactam derivatives is reported. The reaction sequence includes the transformation of chiral furanylazide to a 2S-hydroxymethyldihydro pyridone, which was reduced diasteroselectively, protected and oxidized to two corresponding δ-lactam derivatives. Asymmetric dihydroxylation and oxidation of the latter compounds afforded two chiral (2R,3S)-3-hydroxypipecolic acid δ-lactam derivatives. © 2002 Elsevier Science Ltd. All rights reserved. |
en |
| heal.journalName |
Tetrahedron |
en |
| dc.identifier.issue |
33 |
en |
| dc.identifier.volume |
58 |
en |
| dc.identifier.doi |
10.1016/S0040-4020(02)00674-9 |
en |
| dc.identifier.spage |
6665 |
en |
| dc.identifier.epage |
6671 |
en |