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.

dc.contributor.author	Chandrasoma, Nalin
dc.contributor.author	Brown, Neil
dc.contributor.author	Brassfield, Allen
dc.contributor.author	Nerurkar, Alok
dc.contributor.author	Suarez, Susana
dc.contributor.author	Buszek, Keith R.
dc.date.accessioned	2014-10-24T19:42:37Z
dc.date.available	2014-10-24T19:42:37Z
dc.date.issued	2014-09-30
dc.identifier.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
dc.identifier.uri	http://hdl.handle.net/1808/15383
dc.description	From PMC: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.
dc.description.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.
dc.publisher	Elsevier
dc.subject	Indole
dc.subject	Aryne
dc.subject	Benzofuran
dc.subject	Trikentrin
dc.subject	Herbindole
dc.subject	Natural Prodcuts
dc.subject	Cycloaddition
dc.subject	Total Synthesis
dc.subject	Stille
dc.subject	Cross-coupling
dc.title	Total Synthesis of (±)-Cis-Trikentrin B via Intermolecular 6,7-Indole Aryne Cycloaddition and Stille Cross-Coupling
dc.type	Article
kusw.kuauthor	Brown, Neil
kusw.kuauthor	Buszek, Keith R.
kusw.kudepartment	Chemical Methodologies
kusw.oastatus	fullparticipation
dc.identifier.doi	10.1016/j.tetlet.2012.11.125
kusw.oaversion	Scholarly/refereed, author accepted manuscript
kusw.oapolicy	This item meets KU Open Access policy criteria.
dc.rights.accessrights	openAccess

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