The structure of the unusual anthelmintic pyrrolobenzoxazine terpenoid natural product CJ-12662 was established by X-ray crystallography and partial synthesis from 2-chloronitrobenzene. An unusual Meisenheimer-type rearrangement was used to provide the core pyrrolobenzoxazine heterocycle, and coupling of a tetracyclic pyrrolobenzoxazine lactone with the terpene alcohol was used to complete the synthesis of CJ-12662.
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Biosynthesis of Terpenoid-Pyrrolobenzoxazine Hybrid Natural Product CJ-12662.
Angew Chem Int Ed Engl
March 2022
Department of Chemical and Biomolecular Engineering, University of California, Los Angeles, CA 90095, USA.
The fungal natural product CJ-12662 is a structurally complex terpene-amino acid hybrid, and is a potent anthelmintic compound. The biosynthetic pathway of CJ-12662 is elucidated based on metabolite analysis from heterologous expression. We demonstrate the terpene portion is derived from successive P450-catalyzed oxidations of amorpha-4,11-diene, while three flavin-dependent enzymes are involved in morphing the esterified tryptophan into a chlorinated pyrrolobenzoxazine, utilizing a cascaded [1,2]-Meisenheimer rearrangement.
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Chem Commun (Camb)
November 2004
Department of Chemistry, University of Oxford, Chemical Research Laboratory, UK.
Starting from a protected L-tryptophan derivative the pyrrolobenzoxazine core unit of paeciloxazine can be synthesized in two oxidation steps.
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J Org Chem
November 2004
Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK.
The structure of the unusual anthelmintic pyrrolobenzoxazine terpenoid natural product CJ-12662 was established by X-ray crystallography and partial synthesis from 2-chloronitrobenzene. An unusual Meisenheimer-type rearrangement was used to provide the core pyrrolobenzoxazine heterocycle, and coupling of a tetracyclic pyrrolobenzoxazine lactone with the terpene alcohol was used to complete the synthesis of CJ-12662.
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Research Laboratory Agrochemical & Animal Health Products Department, Kaken Pharmaceutical CO., LTD., 301 Gensuke, Fujieda, Shizuoka 426-8646, Japan.
A novel nematicidal antibiotic, paeciloxazine has been isolated from the culture broth of a fungus Paecilomyces BAUA3058 strain. This compound, whose structure was determined by spectroscopic methods, has a pyrrolobenzoxazine skeleton. Paeciloxazine has moderate cidal activity against Rhabditis pseudoelongata and is weakly active against some insects.
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