Total Synthesis and Stereochemistry of Cytoblastin
| Autor: | Yoshito Kishi, Ofir A. Moreno |
|---|---|
| Rok vydání: | 1996 |
| Předmět: |
Indoles
Lactams Stereochemistry Clinical Biochemistry Pharmaceutical Science chemistry.chemical_element Stereoisomerism Biochemistry Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Structural correlation Drug Discovery Osmium Molecular Biology Organic Chemistry Total synthesis Cytoblastin General Chemistry chemistry Protein kinase C activation Dihydroxylation Carcinogens Molecular Medicine Stereoselectivity Derivative (chemistry) |
| Zdroj: | Journal of the American Chemical Society. 118:8180-8181 |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | The first total synthesis and stereochemical assignment of cytoblastin were reported. Key steps included the palladium-mediated coupling of N-SEM-7-bromoindolactam V ((-)-11) with allylstannane c-13, and osmium tetroxide-mediated dihydroxylation of 14, both of which were stereoselective. The stereochemistry of cytoblastin was determined as 1A via spectroscopic analysis of the pentacyclic derivative 21 of cytoblastin. A connection was then made between the stereochemistry so elucidated and the Kishi/Rando hypothesis for the structural correlation between (S)-1,2-diacylglycerol and tumor promoters for the process of protein kinase C activation. |
| Databáze: | OpenAIRE |
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