The trikentrins and herbindoles are structurally uncommon classes of annulated indole alkaloid natural products. These fascinating and biologically active targets present fantastic synthetic challenges and they continue to be the subject of numerous investigations. An efficient formal total synthesis of (�)-herbindole A and B from a common intermediate was accomplished via intermolecular 6,7-indole aryne cycloaddition methodology followed by Negishi cross-coupling at the C-4 bromine. This tactic is an extension of our previous work on indole aryne and benzofuran aryne cycloadditions (see for example Buszek et al., Org. Lett. 2007 , 9, 4135-4137; Tetrahedron Lett. 2009 , 50, 201-204; Org. Lett. 2009 , 11, 63-65; Tetrahedron Lett. 2009 , 50, 7113-7115; Org. Lett. 2010 , 12, 96-99; ACS Comb. Sci. 2011 , 13, 443-448; Tetrahedron Lett. 2012 , 53, 4022-4025). Synthetic studies towards the total synthesis of (�)-herbindole C are also described.

Synthetic studies towards herbindole A, B, and C via intermolecular 6,7-indole aryne cycloaddition and Negishi cross-coupling reactions

245th National Meeting (2013)

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