Photochemical Synthesis of Indolocarbazoles through Tandem Indolization/Dimerization/Mannich Cyclization from Allenes.

Org Lett

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research and Development of Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, China.

Published: May 2022

Indolocarbazole alkaloids and their derivatives were discovered to have potent protein kinase and topoisomerase I inhibitory activities. Disclosed herein is the photochemical synthesis of the indolocarbazole ring system from -allenyl-2-iodoanilines. The tandem protocol included visible-light-mediated 5--trig radical cyclization and subsequent radical dimerization, followed by acid-promoted deprotection and intramolecular Mannich cyclization. This strategy showed exceptional functional group tolerance and was successfully applied in the concise synthesis of natural products tjipanazoles B and D.

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http://dx.doi.org/10.1021/acs.orglett.2c01371DOI Listing

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