Asymmetric Synthesis of a Hydroxylated Nine-membered Lactone from Tartaric Acid using the Claisen Rearrangement
Leon S-M Wong, Kathleen A Turner, Jonathan M White, Andrew B Holmes, John H Ryan
AUSTRALIAN JOURNAL OF CHEMISTRY | CSIRO PUBLISHING | Published : 2010
The synthesis of a hydroxylated vinyl-appended lactone, in five synthetic steps from tartaric acid, is reported. The C2-symmetrical bis-vinyl diol 12 was converted into the ketene acetal 14 via methylenation of the cyclic carbonate 13 or thermal elimination of benzeneselenenic acid from the selenoxide 17. In both cases, the in situ generated ketene acetal 14 underwent spontaneous Claisen rearrangement to give the nine-membered lactone (+)-15. Lactones of this type are potentially advanced precursors to simplified eleutherobin analogues or other medium-ring lactone natural products. © 2010 CSIRO.
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The authors thank CSIRO (Australia), the Australian Research Council and the Victorian Endowment for Science, Knowledge and Innovation (VESKI) for financial support. We also thank Dr Roger Mulder and Dr Jo Cosgriff for assistance with collection of NMR data and Dr Carl Braybrook for interpretation of MS data.