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Issue 18, 2014
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Complexity generation by chemical synthesis: a five-step synthesis of (−)-chaetominine from L-tryptophan and its biosynthetic implications

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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).

Graphical abstract: Complexity generation by chemical synthesis: a five-step synthesis of (−)-chaetominine from l-tryptophan and its biosynthetic implications

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Publication details

The article was received on 11 Feb 2014, accepted on 13 Feb 2014 and first published on 13 Feb 2014


Article type: Communication
DOI: 10.1039/C4OB00314D
Citation: Org. Biomol. Chem., 2014,12, 2859-2863
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    Complexity generation by chemical synthesis: a five-step synthesis of (−)-chaetominine from L-tryptophan and its biosynthetic implications

    C. Xu, S. Luo, A. Wang and P. Huang, Org. Biomol. Chem., 2014, 12, 2859
    DOI: 10.1039/C4OB00314D

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