Full Stereochemical Assignment and Synthesis of the Potent Anthelmintic Pyrrolobenzoxazine Natural Product CJ-12662

Full Stereochemical Assignment and Synthesis of the Potent Anthelmintic Pyrrolobenzoxazine Natural Product CJ-12662

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 coupli...

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Veröffentlicht in:Journal of organic chemistry 2004-11, Vol.69 (23), p.7875-7879
Hauptverfasser: Didier, Charles, Critcher, Douglas J, Walshe, Nigel D, Kojima, Yasuhiro, Yamauchi, Yuji, Barrett, Anthony G. M
Format: Artikel
Sprache:eng
Schlagworte:
Anthelmintics - chemical synthesis
Anthelmintics - chemistry
Anthelmintics - pharmacology
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiparasitic agents
Benzoxazines - chemical synthesis
Benzoxazines - chemistry
Benzoxazines - pharmacology
Biological and medical sciences
Chemistry
Crystallography, X-Ray
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Medical sciences
Molecular Structure
Organic chemistry
Pharmacology. Drug treatments
Preparations and properties
Pyrroles - chemical synthesis
Pyrroles - chemistry
Pyrroles - pharmacology
Stereoisomerism
Terpenes - chemical synthesis
Terpenes - chemistry
Terpenes - pharmacology
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048711t