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Paper

Org. Biomol. Chem., 2010, 8, 226 - 233, DOI: 10.1039/b918091e

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

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

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.

Graphical abstract image for this article (ID: b918091e)