期刊
TETRAHEDRON
卷 129, 期 -, 页码 -出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2022.133146
关键词
Pallimamine; Tetrahydroberberine; Total synthesis; Formal [4+2] cycloaddition; Mitsunobu reaction
资金
- Welch Foundation
- [E-1916-20170325]
In this study, the synthesis of Pallimamine and its non-natural diastereomer epi-pallimamine was successfully achieved, providing a novel approach for the synthesis of quaternary carbon-containing pentacyclic tetrahydroberberines.
Pallimamine (1) is a structurally unique quaternary carbon-containing pentacyclic tetrahydroberberine. Synthesis of key C13-disubstituted tetrahydroberberine intermediates, as separable diastereomeric iso-mers, was achieved using a formal [4 + 2] cycloaddition of 4-methylhomophthalic anhydrides with 6,7-dimethoxy-3,4-dihydroisoquinolin-8-ol. Intramolecular Mitsunobu reactions provided installation of the dihydropyran generating pallimamine (1) and its non-natural diastereomer epi-pallimamine (33). (c) 2022 Elsevier Ltd. All rights reserved.
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