Synthesis of Alstoscholarisines A–E, Monoterpene Indole Alkaloids with Modulating Effects on Neural Stem Cells
| Autor: | Jeremy D. Mason, Steven M. Weinreb |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Lactams
Stereochemistry Monoterpene Stereoisomerism Acetates 010402 general chemistry 01 natural sciences Aldehyde Catalysis Structure-Activity Relationship chemistry.chemical_compound Neural Stem Cells Humans Structure–activity relationship Indole test chemistry.chemical_classification Aldehydes Molecular Structure 010405 organic chemistry organic chemicals Organic Chemistry Secologanin Tryptamine Alkaloids 0104 chemical sciences Adult Stem Cells chemistry Cyclization Drug Design Michael reaction Aminal Stereoselectivity Oxidation-Reduction |
| Zdroj: | The Journal of Organic Chemistry. 83:5877-5896 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.8b00889 |
| Popis: | A divergent synthetic strategy has been developed for stereoselective total syntheses of alstoscholarisines A-E, monoterpenoid indole alkaloids which are modulators of adult neuronal stem cells. A pivotal step includes an intermolecular Michael addition of an indole-2-acetic acid methyl ester enolate to an α,β-unsaturated N-sulfonyllactam to form the C15, C16 bond of the alkaloids. Other features of the strategy involve a selective partial reduction of an intermediate N-sulfonyllactam followed by cyclization to a bridged aminal system that serves as a key precursor for all five of the alkaloids as well as the use of an allyl group as a masked aldehyde equivalent. |
| Databáze: | OpenAIRE |
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