Synthesis of 1,10-seco-triterpenoids by the Beckmann fragmentation from allobetulin
| Autor: | Maxim V. Dmitriev, Victoria V. Grishko, I. A. Tolmacheva, E. I. Boreko, Alexey V. Nazarov |
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| Rok vydání: | 2017 |
| Předmět: |
010405 organic chemistry
Stereochemistry Organic Chemistry Absolute configuration Stereoisomerism 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Stereocenter chemistry.chemical_compound Triterpenoid chemistry Fragmentation (mass spectrometry) Drug Discovery Beckmann rearrangement Organic chemistry Oleanane |
| Zdroj: | Tetrahedron. 73:6448-6455 |
| ISSN: | 0040-4020 |
| Popis: | A new convenient route to synthesize 1,10-seco-triterpenoids from allobetulin was demonstrated. Stereoisomerism of starting oleanane 1-oximes was determined by X-ray crystallography and additionally confirmed by the structure of the obtained Beckmann rearrangement products. Absolute configuration of chiral centers of 1,10-secotriterpenoids was found to be identical to that of stereocenters in respective precursors. Antiviral activity of 1,10-seco-derivatives was studied against herpes simplex virus type I. |
| Databáze: | OpenAIRE |
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