A biosynthetically-inspired synthesis of the tetrahydrofuran core of obtusallenes II and IV |
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| Authors: | Braddock D Christopher Bhuva Roshni Millan David S Pérez-Fuertes Yolanda Roberts Craig A Sheppard Richard N Solanki Savade Stokes Elaine S E White Andrew J P |
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| Affiliation: | Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, U.K. c.braddock@imperial.ac.uk |
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| Abstract: | [reaction: see text] Sharpless asymmetric dihydroxylation was regioselective for the trans olefin in an E vs Z vs terminal triene substrate. To test a biosynthetic hypothesis, the resulting diol underwent diastereoselective bromoetherification to provide the des-chloro core of marine natural products obtusallenes II and IV. Alternatively, anionic chloride ring-opening of a Z-beta,gamma-unsaturated epoxide gave separable regioisomeric halohydrins. Bromoetherification gave the fully elaborated core of obtusallenes II and IV with all of the relative stereochemistry correctly set. |
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