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Diastereoselective Synthesis of the A-B-C Tricyclic Ring Structure of Stemocurtisine

Dau, Xuan Duc; Willis, Anthony; Pyne, Stephen G

Description

The diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine is described. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide. Attempts to prepare the C-3a-C-11 ether moiety of this alkaloid through a photochemically induced oxidative cyclization method were unsuccessful because of the cleavage of the A-ring.

dc.contributor.authorDau, Xuan Duc
dc.contributor.authorWillis, Anthony
dc.contributor.authorPyne, Stephen G
dc.date.accessioned2016-02-24T22:41:30Z
dc.identifier.issn1434-193X
dc.identifier.urihttp://hdl.handle.net/1885/98711
dc.description.abstractThe diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine is described. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide. Attempts to prepare the C-3a-C-11 ether moiety of this alkaloid through a photochemically induced oxidative cyclization method were unsuccessful because of the cleavage of the A-ring.
dc.publisherWiley-VCH Verlag GMBH
dc.sourceEuropean Journal of Organic Chemistry
dc.titleDiastereoselective Synthesis of the A-B-C Tricyclic Ring Structure of Stemocurtisine
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume2015
dc.date.issued2015
local.identifier.absfor030600 - PHYSICAL CHEMISTRY (INCL. STRUCTURAL)
local.identifier.absfor039900 - OTHER CHEMICAL SCIENCES
local.identifier.ariespublicationU3488905xPUB6849
local.type.statusPublished Version
local.contributor.affiliationDau, Xuan Duc, University of Wollongong
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationPyne, Stephen G, University of Wollongong
local.description.embargo2037-12-31
local.bibliographicCitation.issue35
local.bibliographicCitation.startpage7682
local.bibliographicCitation.lastpage7694
local.identifier.doi10.1002/ejoc.201501080
dc.date.updated2016-02-24T10:12:21Z
local.identifier.scopusID2-s2.0-84948154868
CollectionsANU Research Publications

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