Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids
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Banwell, Martin; Ma, Xinghua; Taylor, Rebecca; Willis, Anthony
Description
Reaction of N-methylindole (4) with 6,6-dibromobicyclo[3.1.0]hexane (5) in the presence of silver tetrafluoroborate affords conjugate 7 in 67% yield. This product can be readily elaborated to compounds 12b and 13b which embody the polycyclic frameworks associated with members of the hapalindole and fischerindole classes of alkaloids. The chiral-auxiliary-substituted 6,6-dibromobicyclo[3.1.0]hexanes 21 and 22 react with indole to give adducts likely to be useful in the enantioselective total...[Show more]
Collections | ANU Research Publications |
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Date published: | 2006 |
Type: | Journal article |
URI: | http://hdl.handle.net/1885/17157 |
Source: | Organic Letters |
DOI: | 10.1021/ol062020x |
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