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ABC → ABCE/D Based Approaches to the Pentacyclic Ring System of the Vinca Alkaloids Using Intramolecular Hetero-[2+2]cycloaddition and Gold(I)-Catalyzed 6-endo-dig Cyclisation Protocols

Willis, Anthony C.; Banwell, Martin G.; White, Lorenzo V.

Description

The angularly substituted tetrahydrocarbazole 13, which is readily obtained from cyclohexane-1,4-dione monoethylene ketal (6) using Fischer indole chemistry, has been converted into the isothiocyanate 16. Photolysis of this last compound affords, via an intramolecular hetero-[2+2]cycloaddition reaction, the pentacyclic "-thiolactam 17 that incorporates the ABCE ring substructure of natural products 1-3. Attempts to effect a two-carbon homologation of the four-membered ring within compound 17,...[Show more]

dc.contributor.authorWillis, Anthony C.
dc.contributor.authorBanwell, Martin G.
dc.contributor.authorWhite, Lorenzo V.
dc.date.accessioned2015-03-10T02:41:59Z
dc.date.available2015-03-10T02:41:59Z
dc.identifier.issn0385-5414)
dc.identifier.urihttp://hdl.handle.net/1885/12864
dc.description.abstractThe angularly substituted tetrahydrocarbazole 13, which is readily obtained from cyclohexane-1,4-dione monoethylene ketal (6) using Fischer indole chemistry, has been converted into the isothiocyanate 16. Photolysis of this last compound affords, via an intramolecular hetero-[2+2]cycloaddition reaction, the pentacyclic "-thiolactam 17 that incorporates the ABCE ring substructure of natural products 1-3. Attempts to effect a two-carbon homologation of the four-membered ring within compound 17, and thereby establish the D-ring, failed. The azide 20, also obtained from compound 13, forms the cyclic imine 21 on thermolysis in refluxing toluene and the readily derived enamide 23 engages in a Au(I)-catalysed 6-endo-dig cyclisation reaction to give compound 24 embodying the ABCDE ring system of the title alkaloids.
dc.description.sponsorshipThis research was funded by the Australian Research Council.
dc.format18 pages
dc.publisherJapan Institute of Heterocyclic Chemistry
dc.rights© Copyright 2015 Elsevier B.V.
dc.sourceHETEROCYCLES
dc.subjecttetrahydrocarbazole 13
dc.subjectisothiocyanate 16
dc.subjectPhotolysis
dc.subjectABCE ring substructure
dc.subjecttwo-carbon homologation
dc.subjectazide 20
dc.subjectcompound 13
dc.titleABC → ABCE/D Based Approaches to the Pentacyclic Ring System of the Vinca Alkaloids Using Intramolecular Hetero-[2+2]cycloaddition and Gold(I)-Catalyzed 6-endo-dig Cyclisation Protocols
dc.typeJournal article
local.identifier.citationvolume90
dc.date.issued2015
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4005981xPUB862
local.publisher.urlhttp://www.elsevier.com/
local.type.statusPublished version
local.contributor.affiliationBanwell, Martin G., Research School of Chemistry, Institute of Advanced Studies, Australian National University
local.contributor.affiliationWhite, Lorenzo V., Research School of Chemistry, Institute of Advanced Studies, Australian National University
local.bibliographicCitation.issue1
local.bibliographicCitation.startpage298
local.bibliographicCitation.lastpage315
local.identifier.doi10.3987/COM-14-S(K)19
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2015-12-10T09:25:22Z
local.identifier.scopusID2-s2.0-84923278762
CollectionsANU Research Publications

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