Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids.
[reaction: see text] 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.
Banwell
Martin G
MG
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia. mgb@rcs.anu.edu.au
Ma
Xinghua
X
Taylor
Rebecca M
RM
Willis
Anthony C
AC
D002384:Catalysis; D006586:Hexanes / Q000737:chemistry; D007202:Indicators and Reagents; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry* / Q000145:classification; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure
D006586:Hexanes; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles; C491991:fischerindole; C022957:1-methylindole