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The first asymmetric total synthesis of natural indole alkaloid (+)-decursivine has been successfully accomplished in 10 steps and a 16.7% overall yield starting from the D-tryptophan derivative.The key step involves the PIFA-mediated intramolecular [3+2] cycloaddition of 5-hydroxytryptophan with a substituted cinnamamide in a highly diastereoselective manner.