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A Raney-cobalt-mediated tandem reductive cyclization route to the 1,5-methanoazocino[4,3-b]indole framework of the uleine and strychnos alkaloids

Reekie, Tristan; Banwell, Martin; Willis, Anthony

Description

The readily accessible enones 8, 17, and 18 undergo 2-fold reductive cyclization reactions upon exposure to hydrogen in the presence of Raney-cobalt and thereby afford compounds 11 (72%), 19 (47%), and 20 (84%), respectively. These products embody the ABCD-ring system associated with the title alkaloids, and compound 11 can be converted, over four steps and in 33% yield, into congener 24 incorporating the ABCDE-ring system of the Strychnos alkaloids.

CollectionsANU Research Publications
Date published: 2012
Type: Journal article
URI: http://hdl.handle.net/1885/69479
Source: Journal of Organic Chemistry
DOI: 10.1021/jo302132d

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