Journal
ORGANIC LETTERS
Volume 24, Issue 19, Pages 3582-3587Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01371
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Funding
- National Natural Science Foundation of China [22061044, 21871228]
- Natural Science Foundation of Yunnan Province [202001BB050038, 2018FY001015]
- Program of Changjiang Scholars and Innovation Research Team in University [IRT17R94]
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The indolocarbazole ring system was synthesized through a photochemical method, demonstrating exceptional functional group tolerance and successfully applied in the concise synthesis of natural products tjipanazoles B and D.
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 N-allenyl-2-iodoanilines. The tandem protocol included visible-light-mediated 5-exo-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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