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Total Synthesis of (−)-Blepharocalyxin D and Analogues

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journal contribution
posted on 19.02.2016 by Benjamin D. Cons, Adam J. Bunt, Christopher D. Bailey, Christine L. Willis
An efficient strategy for the total synthesis of (−)-blepharocalyxin D and an analogue is described. The key step involves an acid-mediated cascade process in which reaction of methyl 3,3-dimethoxypropanoate with γ,δ-unsaturated alcohols possessing diastereotopic styrenyl groups gives trans-fused bicyclic lactones with the creation of two rings and four stereocenters in one pot.