Journal
HETEROCYCLES
Volume 86, Issue 2, Pages 1009-1014Publisher
Japan Inst Heterocyclic Chemistry
DOI: 10.3987/COM-12-S(N)123
Keywords
Total Synthesis; Keramamine C; Amphimedon sp.; Absolute Configuration
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Funding
- Ministry of Education, Science, Sports, and Culture of Japan
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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.
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