SmI(2)-induced reductive cyclizations for the synthesis of cyclic ethers and applications in natural product synthesis.
This tutorial review covers SmI(2)-induced reductive cyclizations of beta-alkoxyacrylate, beta-alkoxyvinyl sulfone, and beta-alkoxyvinyl sulfoxide, as methods for efficient construction of cyclic ethers. These cyclizations were developed as tools to aid in the total synthesis of marine polycyclic ethers, whose complex, synthetically challenging structures and potent bioactivities have attracted the attention of numerous synthetic organic chemists. Applications of the methods to total syntheses of various natural products containing cyclic ether are also described.
Nakata
Tadashi
T
Department of Chemistry, Faculty of Science, Tokyo University of Science, 1-3, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. nakata@rs.kagu.tus.ac.jp
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism
D001688:Biological Products; D004988:Ethers, Cyclic; D007454:Iodides; D012493:Samarium; C409809:samarium diiodide