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Communication | Regular issue | Vol 9, No. 12, 1978, pp.1749-1757
Published online, 1st January, 1970
DOI: 10.3987/R-1978-12-1749
An Approach to the Skeleton of Rauwolfia Alkaloids: A General Synthesis of 3,8-Epoxy-7-keto-6-oxabicyclo[3.2.1]octane Derivatives

Toshio Suzuki, Seiko Kagawa, Akiko Tomino, Katsuo Unno, Tetsuji Kametani,* Tamiko Takahashi, and Yoshihiro Tanaka

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Halolactonization of the Diels-Alder adduct (3a) derived from bis(trimethylsilyl)allene dicarboxylate (2) and furan, followed by a treatment of the products (5a) and (5c) with diazomethane, afforded the corresponding α,β-unsaturated methyl esters (5b) and (5d), respectively. Catalytic hydrogenation of both compounds provided the desired methyl esters (4a) and (4b) which were identical with the compounds derived from Arndt-Eistert reaction of the halolactonic acids (7a) and (7c), respectively.