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

Author
Robertson, Jeremy
Chovatia, Praful T.
Fowler, Thomas G.
Withey, Jonathan
Woollaston, Daniel J.
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