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

Robertson, J., Chovatia, P. T., Fowler, T. G., Withey, J., & Woollaston, D. J. (2010). Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D.
Metadata
TitleOxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D
Author(s)Robertson, Jeremy; Chovatia, Praful T.; Fowler, Thomas G.; Withey, Jonathan; Woollaston, Daniel J.
Date2010
Keyword(s)organic chemistry, enol ethers, spiroacetal
DescriptionTwo 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.
Peer ReviewedYes
Type of ItemJournal Articles
DOIdoi:10.1039/B918091E
Publication InformationRobertson, 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
MacEwan Users Onlyhttp://library.macewan.ca/cgi-bin/SFX/url.pl/7M7
LanguageEnglish
RightsAll Rights Reserved