title: Total Synthesis of (±)-Cis-Trikentrin B via Intermolecular 6,7-Indole Aryne Cycloaddition and Stille Cross-Coupling.
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 cycloadditionviaselective 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.
authors.affiliation: Department of Chemistry, University of Missouri, 205 Kenneth A. Spencer Chemical Laboratories, 5100 Rockhill Road, Kansas City, Missouri 64110, USA.
authors.forename: Nalin
authors.initials: N
authors.lastname: Chandrasoma
authors.affiliation: Department of Chemistry, University of Missouri, 205 Kenneth A. Spencer Chemical Laboratories, 5100 Rockhill Road, Kansas City, Missouri 64110, USA ; Center of Excellence in Chemical Methodologies and Library Development, University of Kansas, Del Shankel Structural Biology Center, 2034 Becker Drive, Lawrence, Kansas 66047, USA.
authors.forename: Neil
authors.initials: N
authors.lastname: Brown
authors.affiliation: Department of Chemistry, University of Missouri, 205 Kenneth A. Spencer Chemical Laboratories, 5100 Rockhill Road, Kansas City, Missouri 64110, USA.
authors.forename: Allen
authors.initials: A
authors.lastname: Brassfield
authors.affiliation: Department of Chemistry, University of Missouri, 205 Kenneth A. Spencer Chemical Laboratories, 5100 Rockhill Road, Kansas City, Missouri 64110, USA.
authors.forename: Alok
authors.initials: A
authors.lastname: Nerurkar
authors.affiliation: Department of Chemistry, University of Missouri, 205 Kenneth A. Spencer Chemical Laboratories, 5100 Rockhill Road, Kansas City, Missouri 64110, USA.
authors.forename: Susana
authors.initials: S
authors.lastname: Suarez
authors.affiliation: Department of Chemistry, University of Missouri, 205 Kenneth A. Spencer Chemical Laboratories, 5100 Rockhill Road, Kansas City, Missouri 64110, USA ; Center of Excellence in Chemical Methodologies and Library Development, University of Kansas, Del Shankel Structural Biology Center, 2034 Becker Drive, Lawrence, Kansas 66047, USA.
authors.forename: Keith R
authors.initials: KR
authors.lastname: Buszek
keywords: Indole; Stille; aryne; benzofuran; cross-coupling; cycloaddition; herbindole; natural products; total synthesis; trikentrin