Work

Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**

Year: 2021

Type: article

Abstract: A complementary dual carbonyl activation strategy for the synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine and 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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202102518

Authors: Guoli He, Benjamin List, Mathias Christmann

Institutions: Freie Universität Berlin, Max-Planck-Institut für Kohlenforschung

Language: English

Topic: Synthesis and bioactivity of alkaloids

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $5,000

Funders: China Scholarship Council, Freie Universität Berlin