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Communication | Special issue | Vol 86, No. 2, 2012, pp.1009-1014
Published online, 5th November, 2012
DOI: 10.3987/COM-12-S(N)123
First Total Synthesis and Absolute Configuration of Keramamine C

Haruaki Ishiyama, Yuta Mori, Takashi Matsumoto, and Jun'ichi Kobayashi*

*Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

Asymmetric first total synthesis of keramamine C, a tetrahydro-β-carboline alkaloid from an Okinawan marine sponge Amphimedon sp., has been accomplished with the Bischler–Napieralski reaction and the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configuration of keramamine C was elucidated to be 1R from comparison of the 1H and 13C NMR, CD spectral data and [α]D values of synthetic and natural keramamine C, respectively.