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Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids

Banwell, Martin; Ma, Xinghua; Taylor, Rebecca; Willis, Anthony


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]

CollectionsANU Research Publications
Date published: 2006
Type: Journal article
Source: Organic Letters
DOI: 10.1021/ol062020x


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