Use of Atom-transfer Radical Cyclizations as an Efficient Entry into a New Serotonergic Norazaadamantane

Document Type

Article

Publication Date

11-24-1992

Publication Title

Tetrahedron Letters

Volume

33

Issue

48

Pages

7283-7286

Publisher Name

Elsevier

Abstract

A route to azanoradamantanes is described which makes use of an atom-transfer radical cyclization to afford 3-azabicyclo[3.3.0]octanes 3A and 3B. Subsequent elaboration of exo-allylamine functionality, followed by cyclization of the endo-hydroxymethyl intermediate 9, affords the new azanoradamantanes 11 and 4. This new azatricyclic system is useful for producing serotonin 5-HT3 antagonists and 5-HT4 agonists.

Comments

Author Posting © Elsevier, 1992. The definitive version was published in Tetrahedron Letters, Volume 33, Issue 48, November 24, 1992. http://dx.doi.org/10.1016/S0040-4039(00)60166-1

Creative Commons License

Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

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