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A three-step synthesis of (±)-harmicine from 3,4-dihydro-β-carboline is achieved by addition of a 3-trimethylsilylpropargyl Grignard reagent, Ag(I)-promoted oxidative cyclization to a pyrrole, and chemoselective hydrogenation of the pyrrole ring.
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Knölker et al. (2004) studied this question.
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