Journal
TETRAHEDRON
Volume 71, Issue 22, Pages 3734-3740Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.07.095
Keywords
Indole alkaloid; Mersicarpine; Indolyl carbinol; Polycyclic indole; Quaternary carbon
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Funding
- National Natural Science Foundation of China [21272225]
- Key Lab of Synthetic Chemistry of Natural Substances, SIOC
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We present an efficient protocol for the Lewis acid-catalyzed reaction of indol-2-yl carbinols with various pi-nucleophiles including the heteroarenes such as indole, pyrrole, furan, as well as the silyl vinyl ethers. Most importantly, the precise use of this protocol enabled us to establish a very concise and practical route for the total synthesis of (+/-)-mersicarpine in eight linear steps with ca. 14% overall yield from commercially available indole and succinic anhydride. Moreover, the method developed herein would be broadly applicable for the diverse synthesis of a number of structurally intriguing indole alkaloids as well as biologically interesting hetero-triarylmethanes. (C) 2014 Elsevier Ltd. All rights reserved.
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