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Paper | Special issue | Vol 88, No. 2, 2014, pp.1323-1336
Published online, 28th August, 2013
DOI: 10.3987/COM-13-S(S)102
Selective Formation of trans/threo/cis and cis/threo/cis Bis-Tetrahydrofurans from the Same Diene Diols

Hiromichi Fujioka,* Tomohiro Oki, Tatsuya Hayashi, Maki Yamakawa, Takeshi Kurachi, Kenji Nakahara, Ryota Maehata, Tomohito Hamada, Kenichi Murai, and Yasuyuki Kita

*Graduate School of Pharmaceutical Science, Osaka University, 1-6 Yamadaoka, Suita, Osaka 560-0871, Japan


Double intramolecular iodoetherification reactions of cyclic acetals and ketals, prepared from the same C2-symmetric diene diol with aldehydes or ketones, stereoselectively afford trans/threo/cis or cis/threo/cis bis-THF ring systems.