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Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D

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dc.contributor.authorRobertson, Jeremy
dc.contributor.authorChovatia, Praful T.
dc.contributor.authorFowler, Thomas G.
dc.contributor.authorWithey, Jonathan M.
dc.contributor.authorWoollaston, Daniel J.
dc.date.accessioned2016-01-12
dc.date.accessioned2022-05-27T01:13:48Z
dc.date.available2022-05-27T01:13:48Z
dc.date.issued2010
dc.description.abstractTwo routes are described for the synthesis of the sawaranospirolides, stereoisomeric spirolactone ascorbigenins isolated from Chamaecyparis pisifera. Trapping of the keto enal formed by oxidation of a functionalised 2-(4-hydroxybutyl)furan affords a potential butenolide spiroacetal precursor to sawaranospirolides A and C. Alternatively, epoxidation of protected 3-(dihydropyran-2-yl)-3-arylpropanoic acids results in spirolactonisation to generate ent-sawaranospirolide C; a related acid-mediated spirocyclisation gave access to ent-sawaranospirolide D.
dc.description.urihttp://library.macewan.ca/cgi-bin/SFX/url.pl/7M7
dc.identifier.citationRobertson, J., Chovatia, P., Fowler, T., Withey, J., & Woollaston, D. (2010). Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D. Organic & Biomolecular Chemistry, 8(1), 226-233. doi:10.1039/B918091E
dc.identifier.doihttps://doi.org/10.1039/B918091E
dc.identifier.urihttps://hdl.handle.net/20.500.14078/281
dc.languageEnglish
dc.language.isoen
dc.rightsAll Rights Reserved
dc.subjectorganic chemistry
dc.subjectenol ethers
dc.subjectspiroacetal
dc.titleOxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and Den
dc.titleOxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and Den
dc.typeArticle

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