Tetrahedron letters

Total synthesis of (±)-cis-trikentrin B via intermolecular 6, 7-indole aryne cycloaddition and Stille cross-coupling

N Chandrasoma, N Brown, A Brassfield, A Nerurkar…

Index: Chandrasoma, Nalin; Brown, Neil; Brassfield, Allen; Nerurkar, Alok; Suarez, Susana; Buszek, Keith R. Tetrahedron Letters, 2013 , vol. 54, # 8 p. 913 - 917

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Citation Number: 17

Abstract

An efficient total synthesis of the annulated indole natural product (±)-cis-trikentrin B was accomplished by means of a regioselectively generated 6, 7-indole aryne cycloaddition via selective metal–halogen exchange from a 5, 6, 7-tribromoindole. The unaffected C-5 bromine was subsequently used for a Stille cross-coupling to install the butenyl side chain and complete the synthesis. This strategy provides rapid access into the trikentrins and the ...