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  • Title: The first total synthesis of discorhabdin A.
    Author: Tohma H, Harayama Y, Hashizume M, Iwata M, Kiyono Y, Egi M, Kita Y.
    Journal: J Am Chem Soc; 2003 Sep 17; 125(37):11235-40. PubMed ID: 16220942.
    Abstract:
    The first stereoselective total synthesis of a potent antitumor alkaloid, discorhabdin A (1), which is a unique sulfur-containing pyrroloiminoquinone alkaloid, is described. The key step in the stereocontrolled total synthesis of 1 involves both a diastereoselective oxidative spirocyclization using a hypervalent iodine(III) reagent and an efficient construction of the labile and highly strained N,S-acetal skeleton. These methodologies provide a breakthrough in the total syntheses of these promising new antitumor agents, discorhabdins and their analogues, which should serve as valuable probes for structure-activity studies.
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