USE OF ATOM-TRANSFER RADICAL CYCLIZATIONS AS AN EFFICIENT ENTRY INTO A NEW "SEROTONERGIC" AZANORADAMANTANE

DOI: 10.1016/S0040-4039(00)60166-1

Source and publish data:

Tetrahedron Letters p. 7283 - 7286 (1992)

Update date:2022-08-05

Topics:

Authors:

Flynn, Daniel L.

Becker, Daniel P.

Nosal, Roger

Zabrowski, Daniel L.

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Article abstract of DOI:10.1016/S0040-4039(00)60166-1

A route to azanoradamantanes is described which makes use of an atom-transfer radical cyclization to afford 3-azabicyclo<3.3.0>ocatanes 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. Key words: Azanoradamantane; 3-azabicyclo<3.3.0>octane; serotonin

Full text of DOI:10.1016/S0040-4039(00)60166-1

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