Towards the total chemical synthesis of the exceptionally potent antibiotic teixobactin, we synthesized the macrocyclic core of a natural product by using a solution‐phase approach. The gramscale synthesis of l‐allo‐enduracididine and Shiina macrolactonization are highlights of the present disclosure.

A simple and practical one-pot, two-directional approach to access olefinic esters through simultaneous breaking and making of olefins using ozonolysis of alkenyl aryl selenides is disclosed. The scope of the method with a variety of examples is demonstrated, and the end products obtained here are useful building blocks. As a direct application of the present method, the macrocyclic core of potent anti-inflammatory natural cyclic peptides, solomonamides, is synthesized.

A highly stereoselective total synthesis of (-)-tirandamycin C has been achieved following a desymmetrization protocol developed in our group, Horner-Wadsworth-Emmons olefination, acid-catalyzed ketalization, Still-Gennari (Z)-selective olefination, and Dieckmann cyclization as key reactions.

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