dc.creator | Bach, Sandra M. | |
dc.creator | Díaz, Fernando R. | |
dc.creator | Bach, Horacio | |
dc.creator | Catalan, Cesar Atilio Nazareno | |
dc.date.accessioned | 2018-07-17T17:15:41Z | |
dc.date.accessioned | 2018-11-06T16:19:48Z | |
dc.date.available | 2018-07-17T17:15:41Z | |
dc.date.available | 2018-11-06T16:19:48Z | |
dc.date.created | 2018-07-17T17:15:41Z | |
dc.date.issued | 2011-04 | |
dc.identifier | Bach, Sandra M.; Díaz, Fernando R.; Bach, Horacio; Catalan, Cesar Atilio Nazareno; A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima; Natural Products; Natural Product Communications; 6; 4; 4-2011; 433-438 | |
dc.identifier | 1934-578X | |
dc.identifier | http://hdl.handle.net/11336/52419 | |
dc.identifier | CONICET Digital | |
dc.identifier | CONICET | |
dc.identifier.uri | http://repositorioslatinoamericanos.uchile.cl/handle/2250/1907099 | |
dc.description.abstract | Enantiomerically pure (+)-vemolepin was semi-synthesized for the first time using the synthon (6S,7R,8S)-8,14-diacetoxy-15-hydroxygermacra-1(10),4,11(13)-trien-6, 12-olide [(+)-minimolide], the major sesquiterpene lactone of the Argentinean vine Mikania minima. After performing four consecutive reactions (Cope rearrangement, two oxidations, and selective hydrolysis of the acetate groups) on the synthon (+)-minimolide, a (+)-vernolepin yield of ca. 40% was achieved, proving to be a suitable semi-synthetic strategy for the production of quantities between 0.5-1.0 g of (+)-vernolepin. The transformations described here mimetize the biogenetic pathway for the production of (+)-vernolepin in the genus Vernonia. The synthesized (+)-vernolepin, but not its precursors, shows antifungal activity similar to amphotericin B. The semi-synthesis reported here combines affordable and easily available chemical reagents with classical organic methodologies. | |
dc.language | eng | |
dc.publisher | Natural Products | |
dc.relation | info:eu-repo/semantics/altIdentifier/url/http://www.naturalproduct.us/JournalArchive.asp | |
dc.rights | https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ | |
dc.rights | info:eu-repo/semantics/restrictedAccess | |
dc.subject | -VERNOLEPINPIN | |
dc.subject | -MINIMOLIDEIDE | |
dc.subject | SEMI-SYNTHESIS | |
dc.subject | ANTIFUNGAL ACTIVITY | |
dc.title | A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima | |
dc.type | Artículos de revistas | |
dc.type | Artículos de revistas | |
dc.type | Artículos de revistas | |