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. 2007 Feb 16;72(4):1405-11.
doi: 10.1021/jo062350v. Epub 2007 Jan 26.

Total synthesis of (+/-)-herbindole A, (+/-)-herbindole B, and (+/-)-cis-trikentrin A

Stephen K Jackson  1 , Michael A Kerr
Affiliations

Total synthesis of (+/-)-herbindole A, (+/-)-herbindole B, and (+/-)-cis-trikentrin A

Stephen K Jackson et al. J Org Chem. .

Abstract

Herein we describe a divergent total synthesis of the title compounds utilizing Diels-Alder reactions of monoimine quinoids, followed by cyclization of the aromatized adducts to generate the tricyclic skeletons. Elaboration to iodinated or triflated indole derivatives allows for installation of the requisite alkyl substitution via cross-coupling reactions.

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