Total synthesis of bioactive canthine alkaloid cordatanine comprising in situ double oxidative aromatization of tetrahydrocarbazole

TitleTotal synthesis of bioactive canthine alkaloid cordatanine comprising in situ double oxidative aromatization of tetrahydrocarbazole
Publication TypeJournal Article
Year of Publication2017
AuthorsShelar, SV, Argade, NP
JournalACS Omega
Volume2
Start Page3945-3950
Issue7
Date PublishedJUL
ISSN2470-1343
Abstract

Starting from tryptamine and methoxymaleic anhydride, concise and efficient total synthesis of cordatanine has been accomplished via regioselective reduction of methoxymaleimide, acid-catalyzed intramolecular cyclization of the formed lactamol, in situ stepwise oxidations leading to aromatization, and intramolecular cyclization with the exchange of N-regioselectivity. An attempted synthesis of regioisomeric natural product zanthochilone has been described in brief with reversal of reduction selectivity. 

DOI10.1021/acsomega.7b00609
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)Not Available
Divison category: 
Organic Chemistry

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