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Communication | Special issue | Vol 72, No. 1, 2007, pp.151-156
Published online, 12th January, 2007
DOI: 10.3987/COM-06-S(K)33
Synthesis of Cyclic Ether via an Intramolecular Barbier Reaction of Iodo Ester with Butyllithium

Tatsuo Saito, Toshiharu Takeuchi, Miyuki Matsuhashi, and Tadashi Nakata*

*Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan


Intramolecular Barbier reaction of 2-(2-iodoethyl)-3-tetrahydropyranyl esters or acyclic 4-iodobutyl ester with t-BuLi or n-BuLi effected cyclization to give six-membered hemiacetals. Based on the present reaction, the synthesis of 2,6-syn-tetrahydropyran and trans-fused polycyclic ethers, and coupling of the AB- and E’FG-rings of gambierol were accomplished.