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A total synthesis of naturally occurring 1-methoxycanthin-6-one is described. In this synthesis, we achieved one-pot conversion from b-carboline-1-carbaldehyde to the canthin-6-one skeleton by the sequential addition of lithium ketene acetal in LiHMDS solution followed by the addition of EtOH in the reaction mixture.
Alkaloids U 0600 Synthetic Studies on Indoles and Related Compounds. Part 53. A Total Synthesis of 1-Methoxycanthin-6-one: An Efficient One-Pot Synthesis of the Canthin-6-one Skeleton from β-Carboline-1-carbaldehyde. -The approach allows an efficient synthesis of the parent compound (IIIa) and the title compound (IIIb). -(SUZUKI*, H.; ADACHI, M.; EBIHARA, Y.; GYOUTOKU, H.; FURUYA, H.; MURAKAMI, Y.; OKUNO, H.; Synthesis 2005, 1, 28-32; Sch. Pharm. Sci., Toho Univ., Funabashi, Chiba 274, Japan; Eng.) -C. Herrmann 21-209
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