A Novel Route to the Fused Maleic Anhydride Moiety of CP Molecules

✍ Scribed by K. C. Nicolaou; Phil S. Baran; Rolf Jautelat; Yun He; Kin Chiu Fong; Ha-Soon Choi; Won Hyung Yoon; Yong-Li Zhong

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 126 KB
• Volume: 38
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/(sici)1521-3773(19990215)38:4<549::aid-anie549>3.0.co;2-o

✦ Synopsis

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.