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Paper | Regular issue | Vol 102, No. 2, 2021, pp.245-253
Published online, 24th December, 2020
DOI: 10.3987/COM-20-14386
Synthesis of Roche Lactone via the Enantioselective Alcoholysis of meso-Cyclic Anhydride Strategy: A Practical Approach Employing an Efficient and Reusable Organic Microgel Auxiliaries

Fei Xiong,* Chang-Cheng Xi, Chao Ma, Lu Chen, Ming-Wei Sun, Xing-Guang Zhang, and Dan-Feng Hong

*Department of Chemistry, University of Shanghai for Science and Technology, Shanghai 200093, China


Roche lactone, a key chiral intermediate of the natural water-soluble B series vitamin (+)-biotin, was synthesized from meso-cyclic anhydride in overall yield 78% through three steps, including heterogeneous asymmetric desymmetrization, chemoselective reduction and lactonization.