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Communication | Special issue | Vol 13, No. 1, 1979, pp.307-320
Published online, 1st January, 1970
DOI: 10.3987/S-1979-01-0307
A New Synthesis of the Synthons for the Functionalized Aspidosperma Alkaloids via α-Ketocarbonium Ion Intermediate

Seiichi Takano,* Kozo Shishido, Jun-ichi Matsuzaka, Masaaki Sato, and Kunio Ogasawara

*Pharmaceutical Institute, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan

Abstract

Acid catalyzed rearrangements of the diazoketones, 14 and 29(a and b) have been examined. On acidic treatments 14 gives the α,β-unsaturated ketone(21), while 29(a and b) give the vinylogous amides 7(a and b) which are converted into the aminoketones 5(a and b), synthons for the synthesis of the functionalized aspidosperma alkaloids, by the dissolving metal reduction.