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Short Paper | Special issue | Vol 99, No. 1, 2019, pp.614-624
Published online, 4th June, 2018
DOI: 10.3987/COM-18-S(F)7
Total Synthesis of Haplacutines B and C

Noriki Kutsumura,* Keisuke Numata, Shiho Mosaki, and Takao Saito*

*Faculty of Science, Department of Chemistry, Tokyo University of Science, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan

Abstract

The total synthesis of 4-quinolone alkaloids, haplacutines B and C, has been achieved. The synthetic highlights are chemoselective construction of a 2-alkyl-4-quinolone skeleton via intramolecular base-promoted cyclocondensation of ortho-alkylamidoacetophenone and stereoselective elongation of the dienol side chain via the Stille coupling.