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Communication | Regular issue | Vol 26, No. 10, 1987, pp.2591-2598
Published online, 1st January, 1970
DOI: 10.3987/R-1987-10-2591
Approach to Natural Occurring α-Methylene Bis-γ-butyrolactones from (R)-1,2,-(O)-Isopropylideneglyceraldehyde as a Chiral Template

Toshio Suzuki, Shinko Kamada, Etsuko Sato, Yasuyuki Matsuda, Katsuo Unno, and Tetsuiji Kametani

*Department of Pharmaceutical Sciences, Akita University Hospital, Hondo, Akita 010, Japan


Both 4-substituted tetrahydrofurano-γ-butyrolactones (12) and (16) which could be key intermedates leading to natural occurring α-methylene bis-γ-butyrolactones were synthesized by regio and stereoselective haloetherification of (8) and (9), followed by a reductive coupling reaction for the preparation of (12), whereas a stereoselective hydrogenation of the enol ether (15) derived from the bromide (14) for the preparation of (16), respectively.