| dc.contributor.author |
Couladourosand, EA |
en |
| dc.contributor.author |
Mihou, AP |
en |
| dc.date.accessioned |
2014-06-06T06:44:00Z |
|
| dc.date.available |
2014-06-06T06:44:00Z |
|
| dc.date.issued |
1999 |
en |
| dc.identifier.issn |
00404039 |
en |
| dc.identifier.uri |
http://dx.doi.org/10.1016/S0040-4039(99)00895-3 |
en |
| dc.identifier.uri |
http://62.217.125.90/xmlui/handle/123456789/1621 |
|
| dc.subject.other |
6 acetoxyhexadecanolide |
en |
| dc.subject.other |
carbonic acid derivative |
en |
| dc.subject.other |
carbonic acid ester |
en |
| dc.subject.other |
delta valerolactone |
en |
| dc.subject.other |
gamma butyrolactone |
en |
| dc.subject.other |
lactone derivative |
en |
| dc.subject.other |
muricatacin |
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.title |
A general synthetic route towards γ- and δ-lactones. Total asymmetric synthesis of (-)-muricatacin and the mosquito oviposition pheromone (5R, 6s)- 6-acetoxy-hexadecanolide |
en |
| heal.type |
journalArticle |
en |
| heal.identifier.primary |
10.1016/S0040-4039(99)00895-3 |
en |
| heal.publicationDate |
1999 |
en |
| heal.abstract |
Five (or six) membered asymmetric lactones are synthesized from γ- butyrolactone (or δ-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. |
en |
| heal.journalName |
Tetrahedron Letters |
en |
| dc.identifier.issue |
26 |
en |
| dc.identifier.volume |
40 |
en |
| dc.identifier.doi |
10.1016/S0040-4039(99)00895-3 |
en |
| dc.identifier.spage |
4861 |
en |
| dc.identifier.epage |
4862 |
en |