Total synthesis of bioactive canthine alkaloid cordatanine comprising in situ double oxidative aromatization of tetrahydrocarbazole
Title | Total synthesis of bioactive canthine alkaloid cordatanine comprising in situ double oxidative aromatization of tetrahydrocarbazole |
Publication Type | Journal Article |
Year of Publication | 2017 |
Authors | Shelar, SV, Argade, NP |
Journal | ACS Omega |
Volume | 2 |
Start Page | 3945-3950 |
Issue | 7 |
Date Published | JUL |
ISSN | 2470-1343 |
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. |
DOI | 10.1021/acsomega.7b00609 |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | Not Available |
Divison category:
Organic Chemistry
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