| dc.contributor.author |
Couladouros, EA |
en |
| dc.contributor.author |
Mihou, AP |
en |
| dc.date.accessioned |
2014-06-06T06:43:49Z |
|
| dc.date.available |
2014-06-06T06:43:49Z |
|
| dc.date.issued |
1999 |
en |
| dc.identifier.issn |
0040-4039 |
en |
| dc.identifier.uri |
http://62.217.125.90/xmlui/handle/123456789/1481 |
|
| dc.subject.classification |
Chemistry, Organic |
en |
| dc.subject.other |
ATTRACTANT PHEROMONE |
en |
| dc.subject.other |
STEREOSELECTIVE SYNTHESIS |
en |
| dc.subject.other |
ENANTIOSELECTIVE SYNTHESIS |
en |
| dc.subject.other |
ANNONACEOUS ACETOGENINS |
en |
| dc.subject.other |
(+)-MURICATACIN |
en |
| dc.subject.other |
ENANTIOMERS |
en |
| dc.subject.other |
BUTYROLACTONES |
en |
| dc.subject.other |
MURICATACIN |
en |
| dc.subject.other |
ALDEHYDES |
en |
| dc.title |
A general synthetic route towards gamma- and delta-lactones. Total asymmetric synthesis of (-)-muricatacin and the mosquito oviposition pheromone (5R,6S)-6-acetoxy-hexadecanolide. |
en |
| heal.type |
journalArticle |
en |
| heal.language |
English |
en |
| heal.publicationDate |
1999 |
en |
| heal.abstract |
Five (or six) membered asymmetric lactones are synthesized from gamma-butyrolactone (or delta-valerolactone) in a straightforward way using the following reaction sequence: reduction, Wittig-Schlosser coupling, Sharpless asymmetric dihydroxylation, oxidation and lactonization. Thus, (-)-muricatacin is synthesized in six steps (43 % overall yield). Furthermore, (5R,6S)-6-acetoxy-hexadecanolide is prepared in eight steps (38 % overall yield) via a carbonate ester, utilizing a novel lactonization with inversion of stereochemistry. (C) 1999 Elsevier Science Ltd. All rights reserved. |
en |
| heal.publisher |
PERGAMON-ELSEVIER SCIENCE LTD |
en |
| heal.journalName |
TETRAHEDRON LETTERS |
en |
| dc.identifier.issue |
26 |
en |
| dc.identifier.volume |
40 |
en |
| dc.identifier.isi |
ISI:000081122200030 |
en |
| dc.identifier.spage |
4861 |
en |
| dc.identifier.epage |
4862 |
en |