The orthoester Johnson–Claisen rearrangement, an important C–C bond forming reaction, has been used enormously in the past four decades in the synthesis of bioactive molecules, natural products, synthetic intermediates, analogues, and useful building blocks. The method has also featured in chemical modification of materials. This review covers developments in this rearrangement since 2003. Unlike many other forms of Claisen rearrangement, this reaction is generally a one‐pot, one‐step process. It is compatible with numerous functional groups, despite its use of acid catalysis, and offers chirality transfer to produce stereoselective products. The method also offers opportunities for rapid modifications to various functionalized compounds and building blocks for further synthetic exploration.

β-Carboline containing alkaloids are ubiquitously present in Nature, while an imidazo[1,2-a]pyridine nucleus is incorporated in various synthetic commercial drugs and biologically previliged moieties.

The total syntheses of all stereoisomers of phenatic acid B and determination of their absolute configuration are described. The synthetic strategy is based on an efficient combination of the Sharpless asymmetric dihydroxylation, the Johnson-Claisen rearrangement, and hydroboration-oxidation. It involves 11-12 steps and overall yield of 5-8%.

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An efficient synthesis of (–)‐(R)‐ and (+)‐(S)‐lavandulol, (+)‐lavandulyl 2‐methylbutanoate and (+)‐lavandulyl senecioate is presented in this paper. The synthetic strategy features a chiral‐pool approach to an allyl alcohol intermediate, and an orthoester Johnson–Claisen rearrangement as the key step.