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  • Title: Complexity generation by chemical synthesis: a five-step synthesis of (-)-chaetominine from L-tryptophan and its biosynthetic implications.
    Author: Xu CP, Luo SP, Wang AE, Huang PQ.
    Journal: Org Biomol Chem; 2014 May 14; 12(18):2859-63. PubMed ID: 24675877.
    Abstract:
    We demonstrated, for the first time, that on the basis of chemistry principles, the hexacyclic peptidyl alkaloid (−)-chaetominine (1) can be synthesized in a straightforward manner from L-Trp. The approach features the efficient generation of molecular complexity via a tandem C3/C14 syn-selective epoxidation (dr = 3:2)–annulative ring-opening reaction and a regioselective epimerization at C14. The successful production of (−)-chaetominine (1) from L-Trp could be helpful for revealing how the configuration of L-tryptophan becomes inverted in the biosynthetic pathway of (−)-chaetominine (1).
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