Studies toward the Synthesis of Lepadiformine A
| Autor: | Sergey V. Tsukanov, Daniel L. Comins, Lucas R. Marks |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Molecular Structure
010405 organic chemistry Chemistry Stereochemistry Proton Magnetic Resonance Spectroscopy Organic Chemistry Stereoisomerism 010402 general chemistry Cleavage (embryo) Ring (chemistry) 01 natural sciences Pyrrolidine 0104 chemical sciences Stereocenter chemistry.chemical_compound Alkaloids Cyclization Lepadiformine Molecule Animals Urochordata Carbon-13 Magnetic Resonance Spectroscopy |
| Zdroj: | The Journal of organic chemistry. 81(21) |
| ISSN: | 1520-6904 |
| Popis: | Herein is described an original approach to access a tricyclic framework of the lepadiformine-type alkaloids. A Grignard/N-acylpyridinium salt reaction of a 4-methoxytetrahydroquinoline is the key carbon–carbon bond-forming step that was used to establish the desired absolute stereochemistry at the C2 position of the target alkaloid. The synthesis features an allylation reaction with an N-acyliminium ion to set the C10 quaternary stereocenter, a mild dissolving-metal cleavage of hindered phenyl carbamates, and an aminoiodocyclization to form the pyrrolidine ring. While this route does not provide the correct C10 stereochemistry, it showcases an efficient method to build analogues with the ring system of this class of alkaloids in 11 steps overall. |
| Databáze: | OpenAIRE |
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