Photochemical Synthesis of Indolocarbazoles through Tandem Indolization/Dimerization/Mannich Cyclization from Allenes
Jiaying Tang1, Linlin Ren1, Jianwei Li1
1Key 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.
Abstract:
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.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
07:12Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Related Concept Videos
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Thermal and Photochemical Electrocyclic Reactions: Overview
Cycloaddition Reactions: MO Requirements for Photochemical Activation
