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  • Title: Total synthesis of (-)-martinellic acid via radical addition-cyclization-elimination reaction.
    Author: Shirai A, Miyata O, Tohnai N, Miyata M, Procter DJ, Sucunza D, Naito T.
    Journal: J Org Chem; 2008 Jun 20; 73(12):4464-75. PubMed ID: 18473441.
    Abstract:
    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(3)SnH-promoted radical addition-cyclization-elimination (RACE) reaction of an oxime ether with an alpha,beta-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 SmI(2). (-)-Martinellic acid was synthesized from commercially available methyl 4-bromo-3-methylbenzoate in fewer steps than previous syntheses and in an improved overall yield.
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