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Total Synthesis of Bioactive Canthine Alkaloid Cordatanine Comprising in Situ Double Oxidative Aromatization of Tetrahydrocarbazole.

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.

SUBMITTER: Shelar SV

PROVIDER: S-EPMC6641036 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Total Synthesis of Bioactive Canthine Alkaloid Cordatanine Comprising in Situ Double Oxidative Aromatization of Tetrahydrocarbazole.

Shelar Santosh V SV Argade Narshinha P NP

ACS omega 20170726 7

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 sele ...[more]

PMID: 31457698

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