| dc.contributor.author |
Couladouros, EA |
en |
| dc.contributor.author |
Magos, AD |
en |
| dc.date.accessioned |
2014-06-06T06:46:41Z |
|
| dc.date.available |
2014-06-06T06:46:41Z |
|
| dc.date.issued |
2005 |
en |
| dc.identifier.issn |
13811991 |
en |
| dc.identifier.uri |
http://dx.doi.org/10.1007/s11030-005-1294-x |
en |
| dc.identifier.uri |
http://62.217.125.90/xmlui/handle/123456789/3136 |
|
| dc.subject |
2,5-diketopiperazines |
en |
| dc.subject |
Amino acids |
en |
| dc.subject |
Horner-Emmons reaction |
en |
| dc.subject |
Natural products |
en |
| dc.subject |
Ylides |
en |
| dc.subject.other |
amine |
en |
| dc.subject.other |
amino acid |
en |
| dc.subject.other |
aurantiamine |
en |
| dc.subject.other |
benzene derivative |
en |
| dc.subject.other |
ester derivative |
en |
| dc.subject.other |
glycine derivative |
en |
| dc.subject.other |
indole |
en |
| dc.subject.other |
phenylhistine |
en |
| dc.subject.other |
phosphine derivative |
en |
| dc.subject.other |
piperazine derivative |
en |
| dc.subject.other |
unclassified drug |
en |
| dc.subject.other |
article |
en |
| dc.subject.other |
drug structure |
en |
| dc.subject.other |
drug synthesis |
en |
| dc.subject.other |
Horner Wadsworth Emmons reaction |
en |
| dc.subject.other |
priority journal |
en |
| dc.subject.other |
racemization |
en |
| dc.subject.other |
Indicators and Reagents |
en |
| dc.subject.other |
Molecular Conformation |
en |
| dc.subject.other |
Molecular Structure |
en |
| dc.subject.other |
Piperazines |
en |
| dc.subject.other |
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization |
en |
| dc.subject.other |
Stereoisomerism |
en |
| dc.title |
Total asymmetric synthesis of (-)-Phenylhistine, (-)-Aurantiamine and related compounds. Part I |
en |
| heal.type |
journalArticle |
en |
| heal.identifier.primary |
10.1007/s11030-005-1294-x |
en |
| heal.publicationDate |
2005 |
en |
| heal.abstract |
A new general, short, and efficient strategy for the construction of dehydro-diketopiperazines was developed. Horner-Emmons type coupling between a phosphinyl glycine ester and a formyl heterocycle is the key coupling reaction, which proceeds in good-to-excellent yields on several sterically-hindered substrates. Moreover, racemization of the parent L-amino acids is avoided as a result of the mild basic conditions used. The selection of the NH protective group of the formyl heterocycle was crucial. N-tosylated heterocycles proved ideal for this reaction sequence. Thus, the title compounds, (-)-Phenylhistine and (-)-Aurantiamine, were prepared in high yield (four steps, 47% overall) and optical purity. Furthermore, the synthesis of unnatural derivatives including an indole analogue was successfully completed. © Springer 2005. |
en |
| heal.journalName |
Molecular Diversity |
en |
| dc.identifier.issue |
1-3 |
en |
| dc.identifier.volume |
9 |
en |
| dc.identifier.doi |
10.1007/s11030-005-1294-x |
en |
| dc.identifier.spage |
99 |
en |
| dc.identifier.epage |
109 |
en |