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

TETRAHEDRON LETTERS

卷:54

Article

Chandrasoma, Nalin¹  Brown, Neil^1,2  Brassfield, Allen¹  Nerurkar, Alok¹  Suarez, Susana¹  Buszek, Keith R.^1,2 

[1] Univ Missouri, Dept Chem, Kenneth A Spencer Chem Labs 205, Kansas City, MO 64110 USA

[2] Univ Kansas, Ctr Excellence Chem Methodol & Lib Dev, Del Shankel Struct Biol Ctr, Lawrence, KS 66047 USA

关键词: Indole;    Aryne;    Benzofuran;    Trikentrin;    Herbindole;    Natural products;    Cycloaddition;    Total synthesis;    Stille;    Cross-coupling;   

DOI  :  10.1016/j.tetlet.2012.11.125

来源: Elsevier

【 摘 要 】

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 related herbindoles, and represents another application of this methodology to natural products total synthesis. The required 5,6,7-indole aryne precursor was prepared using the Leimgruber-Batcho indole synthesis. (C) 2012 Elsevier Ltd. All rights reserved.

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