Oxidative spirocyclisation routes towards the sawaranospirolides. Synthesis of ent-sawaranospirolides C and D
Faculty Advisor
Date
2010
Keywords
organic chemistry, enol ethers, spiroacetal
Abstract (summary)
Two 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.
Publication Information
Robertson, 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
Notes
Item Type
Article
Language
English
Rights
All Rights Reserved