Shiina benzoic anhydride method

2-hydroxy-24-oxooctacosanolide (35) [53], F-labeled antibiotic amphotericin B methyl ester (36) [54], and antimycin Ajj, (8) [55] were effectively synthesized by MNBA combined with the DMAP or DM APO catalyst. Notably, for the preparation of the nine-membered dilactone [37] in the total synthesis of antimycin A31, (8) by Wu [55], efficiency of Shiina MNBA lactonization for the formation of the medium-sized ring core was comprehensively evaluated by a detailed comparison with other estabtished lactonization methods. 

The remarkable efficiency of Shiina lactonization, which was mediated by acyl-transfer catalysts with MNBA, has been already demonstrated in a variety of successful total syntheses of natural products and biologically active compounds by other researchers (totaling over 370 citations to date). Furthermore, over 900 successful reactions using MNBA have been reported for the preparation of a variety of substrates including ester, amide, and lactone moieties. 

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Shiina I (2004) An effective method for the synthesis of carboxylic esters and lactones using substituted benzoic anhydrides with Lewis acid catalysts. Tetrahedron 60 1587-1599... 

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