Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 18, Pages 6059-6063Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201901074
Keywords
alkaloids; cascade reaction; photoredox catalysis; total synthesis; transition metal
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Funding
- National Natural Science Foundation of China [21732005]
- National Science and Technology Major Projects for Major New Drugs Innovation and Development [2018ZX09711003-015, 2017ZX09101003-005-004]
- Fundamental Research Funds for the Central Universities [2012017yjsy103]
- 13CNMR spectra of rhazinoline
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Strictamine and rhazinoline are representative methanoquinolizidine-containing akuammiline alkaloids that possess different stereochemistry at the C16 position. A unified approach to the enantioselective total syntheses of these two molecules is described. The key steps in this synthesis include a photocatalytic intra/intermolecular type II radical cascade reaction, a Tsuji-Trost allylation, a palladium- or nickel-mediated cyclization, and a late-stage intramolecular N-alkylation reaction.
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