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2-(Het)aryl-Substituted 7-Azabicyclo[2.2.1]heptane Systems

✍ Scribed by Albert Otten; Jan Christoph Namyslo; Martin Stoermer; Dieter E. Kaufmann

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
321 KB
Volume
1998
Category
Article
ISSN
1434-193X

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✦ Synopsis

Epibatidine (1) is a recently discovered trace alkaloid found pyrrole (7) with ethynyl p-tolyl sulfone (6) and subsequent steps has been optimized. The crucial last step, the reductive in the skin of a Latin-American poisonous frog. Its remarkably high analgetic activity is accompanied by high cleavage of the vinyl sulfone 9, has been replaced by a highyield fluoride-induced degradation of the Ξ²-silylated sulfone toxicity. Therefore, in order to tune its biological activity, a convergent and efficient synthetic pathway was sought to 12 to give 10. A number of structurally different racemic epibatidine analogs (16b-e) can be prepared by palladium-synthesize epibatidine derivatives with different (het)aryl substituents. The hydro(het)arylation of the key intermediate catalyzed hydro(het)arylation of 10 with iodo(het)arenes 15b-e in good yields. 7-azabicycloheptene (10) represents such an approach. The synthesis of 10 by a Diels-Alder reaction of an N-activated

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: Chemistry in the Am
ChemInform Abstract: Chemistry in the Ambient Field of the Alkaloid Epibatidine. Part 1. 2-(Het)aryl-substituted 7-Azabicyclo[2.2.1]heptane Systems.
✍ A. OTTEN; J. C. NAMYSLO; M. STOERMER; D. E. KAUFMANN πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 32 KB πŸ‘ 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a β€œFull Text” option. The original article is trackable v

Absolute Configuration of 3-Substituted
Absolute Configuration of 3-Substituted 1-Azabicyclo[2.2.1]heptanes
✍ Jakob Boelsterli; Ursula Eggnauer; Esteban Pombo-Villar; Hans-Peter Weber; Malco πŸ“‚ Article πŸ“… 1992 πŸ› John Wiley and Sons 🌐 German βš– 396 KB

The l-azabicyclo[2.2. I]heptan-3-exo-ol (2) was resolved by fractional crystallisation of its hydrogen tartrate salts. The enantiomers (+)-and (-)-2 were oxidised to the ketones (-)-4 and (+)-4, respectively (Scheme). CD spectroscopy suggested that (-)-4 possesses the (IR,4S)-configuration. This abs