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A Novel Route to the Fused Maleic Anhydride Moiety of CP Molecules
Authors:K. C. Nicolaou  Phil S. Baran  Rolf Jautelat  Yun He  Kin Chiu Fong  Ha‐Soon Choi  Won Hyung Yoon  Yong‐Li Zhong
Abstract:A seven‐step cascade reaction —in which selective mesylation, epoxide formation, epoxide lysis, cyclization, reiterative oxidation, and nitrogen–oxygen exchange occur sequentially—facilitates the construction of the maleic anhydride moiety of CP molecules 1 and 2 (>93% yield per step). Unstable intermediates of this reaction sequence were detected, providing evidence for the proposed mechanism and resulting in the discovery of a new chemical entity.
Keywords:Antibiotics  Autoxidation  Cyclizations  Domino reactions  Intermediates
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