FIRST TOTAL SYNTHESIS AND ABSOLUTE CONFIGURATION OF KERAMAMINE C

Asymmetric first total synthesis of keramamine C, a tetrahydro-beta-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 H-1 and C-13 NMR, CD spectral data and [alpha](D), values of synthetic and natural keramamine C, respectively.