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ChemRxiv Alkaloids.pdf (17.37 MB)

Unified Synthesis of Polycyclic Alkaloids via Complementary Carbonyl Activation

preprint
submitted on 18.02.2021, 14:51 and posted on 19.02.2021, 12:54 by Guoli He, Benjamin List, Mathias Christmann
A complementary dual carbonyl activation strategy for the
synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine, harmalacinine, pentacyclic indoloquinolizidine alkaloid nortetoyobyrine, and octacyclic β-carboline alkaloid peganumine A. The latter synthesis features a protecting-group-free assembly and an asymmetric disulfonimide catalyzed cyclization. Furthermore, formal syntheses of hirsutine, deplancheine, 10-desbromoarborescidine A, and oxindole alkaloids rhynchophylline and isorhynchophylline have been achieved. Finally, a concise synthesis of berberine alkaloid ilicifoline B was completed.

Funding

Chinese Scholarship Council

History

Email Address of Submitting Author

mathias.christmann@fu-berlin.de

Institution

Freie Universität Berlin

Country

Germany

ORCID For Submitting Author

0000-0001-9313-2392

Declaration of Conflict of Interest

No conflict of interest.