| dc.contributor.author |
Couladouros, EA |
en |
| dc.contributor.author |
Soufli, IC |
en |
| dc.contributor.author |
Moutsos, VI |
en |
| dc.contributor.author |
Chadha, RK |
en |
| dc.date.accessioned |
2014-06-06T06:43:46Z |
|
| dc.date.available |
2014-06-06T06:43:46Z |
|
| dc.date.issued |
1998 |
en |
| dc.identifier.issn |
09476539 |
en |
| dc.identifier.uri |
http://62.217.125.90/xmlui/handle/123456789/1439 |
|
| dc.relation.uri |
http://www.scopus.com/inward/record.url?eid=2-s2.0-0031884945&partnerID=40&md5=72dc6349158f2d37ad705935c69297b6 |
en |
| dc.subject |
Asymmetric synthesis |
en |
| dc.subject |
Combretastatins |
en |
| dc.subject |
Lactones |
en |
| dc.subject |
Macrocycles |
en |
| dc.subject |
Natural products |
en |
| dc.subject |
Total synthesis |
en |
| dc.title |
Total synthesis of combretastatins D |
en |
| heal.type |
journalArticle |
en |
| heal.publicationDate |
1998 |
en |
| heal.abstract |
The 15-membered caffrane ring of the natural product group of combretastatins D is synthesized in high yield with suitably functionalized saturated seco acids. The key step is a Mitsunobu-type macrolactonization. A common synthon is used for the construction of both combretastatins. The synthesis of combretastatin D-2 is completed by the use of Sammuelson's dehydroxylation protocol. The asymmetric epoxide of combretastatin D-1 is constructed in two separate operations: one asymmetric center is fixed at an early stage of the synthetic route by Sharpless AD of a trans-styrene derivative, inducing the intramolecular formation of the asymmetric epoxide at the final stages. The synthesis of the title compounds is accomplished in high overall yields (37% for D-1 and 41% for D-2, 9 steps in both cases). X-ray crystallographic analysis of the (S)-(+)-acetylmandelic ester of (-)-combretastatin D-1 verified its revised structure. |
en |
| heal.journalName |
Chemistry - A European Journal |
en |
| dc.identifier.issue |
1 |
en |
| dc.identifier.volume |
4 |
en |
| dc.identifier.spage |
33 |
en |
| dc.identifier.epage |
43 |
en |