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Paper | Special issue | Vol 97, No. 2, 2018, pp.1050-1067
Published online, 24th April, 2018
DOI: 10.3987/COM-18-S(T)88
Preparation of Chiral Right-Half Models of Antitumor Bistetrahydroisoquinolinequinone Natural Products

Yuuki Senbonmatsu, Shinya Kimura, Megumi Akiba, Shingo Ando, and Naoki Saito*

*Department of Medicinal Chemistry, Pharmaceutical Chemistry, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

The preparation of chiral right-half model compounds of bistetrahydroisoquinolinequinone natural products having a lactam carbonyl group (-)-1 or an aminonitrile group (+)-2 from (-)-14 was presented. The crucial steps of this synthesis include the N-methylation of compound (-)-12 and ring closure to generate (-)-19a without any epimerization at C-2.