ol062020x_si_004.cif (50.15 kB)

Concise Assembly of the Polycyclic Frameworks Associated with the Hapalindole and Fischerindole Alkaloids

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posted on 12.10.2006, 00:00 by Martin G. Banwell, Xinghua Ma, Rebecca M. Taylor, Anthony C. Willis
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 synthesis of the title alkaloids.