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Total Synthesis of (±)-Cis-Trikentrin B via Intermolecular 6,7-Indole Aryne Cycloaddition and Stille Cross-Coupling
Chandrasoma, Nalin Brown, Neil Brassfield, Allen Nerurkar, Alok Suarez, Susana Buszek, Keith R.
Chandrasoma, Nalin
Brown, Neil
Brassfield, Allen
Nerurkar, Alok
Suarez, Susana
Buszek, Keith R.
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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 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.
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Date
2014-09-30
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Elsevier
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Keywords
Indole, Aryne, Benzofuran, Trikentrin, Herbindole, Natural Prodcuts, Cycloaddition, Total Synthesis, Stille, Cross-coupling
Citation
Total Synthesis of (±)-Cis-Trikentrin B via Intermolecular 6,7-Indole Aryne Cycloaddition and Stille Cross-Coupling
Nalin Chandrasoma, Neil Brown, Allen Brassfield, Alok Nerurkar, Susana Suarez, Keith R. Buszek
Tetrahedron Lett. Author manuscript; available in PMC 2014 September 30.
Published in final edited form as: Tetrahedron Lett. 2013 February 20; 54(8): 913–917. http://dx.doi.org.10.1016/j.tetlet.2012.11.125