A biosynthetically-inspired synthesis of the tetrahydrofuran core of obtusallenes II and IV

…, Y Pérez-Fuertes, CA Roberts, RN Sheppard…

Index: Braddock, D. Christopher; Bhuva, Roshni; Millan, David S.; Perez-Fuertes, Yolanda; Roberts, Craig A.; Sheppard, Richard N.; Solanki, Savade; Stokes, Elaine S. E.; White, Andrew J. P. Organic Letters, 2007 , vol. 9, # 3 p. 445 - 448

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Citation Number: 31

Abstract

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-β, γ- unsaturated epoxide gave separable regioisomeric halohydrins. Bromoetherification gave ...