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Chemoenzymatic total syntheses of ribisins A, B and D, polyoxygenated benzofuran derivatives displaying NGF-potentiating properties

Lan, Ping; Banwell, Martin; Willis, Anthony

Description

Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was...[Show more]

dc.contributor.authorLan, Ping
dc.contributor.authorBanwell, Martin
dc.contributor.authorWillis, Anthony
dc.date.accessioned2015-12-10T23:07:53Z
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/63051
dc.description.abstractTotal syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was shown to be represented by 31 rather than 2.
dc.publisherAmerican Chemical Society
dc.sourceJournal of Organic Chemistry
dc.titleChemoenzymatic total syntheses of ribisins A, B and D, polyoxygenated benzofuran derivatives displaying NGF-potentiating properties
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume79
dc.date.issued2014
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4005981xPUB764
local.type.statusPublished Version
local.contributor.affiliationLan, Ping, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationBanwell, Martin, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue7
local.bibliographicCitation.startpage2829
local.bibliographicCitation.lastpage2842
local.identifier.doi10.1021/jo500210k
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2015-12-10T09:02:46Z
local.identifier.scopusID2-s2.0-84898067520
local.identifier.thomsonID000334016500003
CollectionsANU Research Publications

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