Total synthesis of (-)-martinellic acid via radical addition-cyclization- elimination reaction

Atsushi Shirai, Okiko Miyata, Norimitsu Tohnai, Mikiji Miyata, David J. Procter, David Sucunza, Takeaki Naito

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    (Chemical Equation Presented) The asymmetric total synthesis of martinellic acid, the first pyrrolo[3,2-c]quinoline alkaloid found in nature, is described. Three key steps in our synthesis of (-)-martinellic acid are the Bu 3SnH-promoted radical addition-cyclization-elimination (RACE) reaction of an oxime ether with an α,β-unsaturated ester to generate the pyrrolo[3,2-c]quinoline core, a chemoselective lactam carbonyl reduction, and guanidinylation under Mitsunobu reaction conditions. The key radical cyclization has also been investigated by using SmI2. (-)-Martinellic acid was synthesized from commercially available methyl 4-bromo-3- methylbenzoate in fewer steps than previous syntheses and in an improved overall yield. © 2008 American Chemical Society.
    Original languageEnglish
    Pages (from-to)4464-4475
    Number of pages11
    JournalJournal of Organic Chemistry
    Issue number12
    Publication statusPublished - 20 Jun 2008


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