Synthetic Studies Towards (-) Mesembrine
| Autor: | Mohamed A. Albadry, Ikhlas A. Khan, Pradeep B. Lasonkar, Amar G. Chittiboyina, SC Rotte |
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| Rok vydání: | 2016 |
| Předmět: |
Pharmacology
Stereochemistry Organic Chemistry Pharmaceutical Science Oxazoline Analytical Chemistry Stereocenter chemistry.chemical_compound Complementary and alternative medicine chemistry Aldol reaction Intramolecular force Drug Discovery Michael reaction Molecular Medicine Moiety Carbene Mesembrine |
| Zdroj: | Planta Medica. 82 |
| ISSN: | 1439-0221 0032-0943 |
| DOI: | 10.1055/s-0036-1578708 |
| Popis: | Mesembrine is a naturally occurring alkaloid which has been isolated from Sceletium tortosum, family Aizoaceae. It has a therapeutic value in the treatment of depression as selective serotonin reuptake inhibitor. Because of its challenging chemical features such as a cis-3a-aryloctahydroindole moiety with syn configuration at two bridge-head stereogenic centers. [1] Several synthetic studies have been published to control the construction of the sterically hindered, benzylic quaternary stereogenic center at C-3a. [2] By utilizing Michael addition on chiral enolate derived from benzyl oxazoline, the desired stereogenic center at carbon 3a was created early in the synthesis followed by carbene insertion and intramolecular aldol reactions to complete the aryloctahydroindole scaffold. The complete details of synthetic transformations will be discussed. Acknowledgements: This research is supported in part by The United States Department of Agriculture, Agricultural Research Service, Specific Cooperative Agreement No. 58 – 6408 – 1-603 – 07 References: [1] K. Geoghegan, P. Evans, The Journal of Organic Chemistry 2013, 78, 3410 – 3415.; [2a] D. F. Taber, T. D. Neubert, The Journal of Organic Chemistry 2001, 66, 143 – 147; [2b] S. P. Chavan, D. A. Khobragade, A. B. Pathak, U. R. Kalkote, Tetrahedron Letters 2004, 45, 5263 – 5265. |
| Databáze: | OpenAIRE |
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