Total Syntheses of Epothilones B and D
| Autor: | Yansong Zheng, Muralikrishna Valluri, Mitchell A. Avery, Rajashaker Kache, Panicker Bijoy, Jae-Chul Jung, Kimberly K. Vines |
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| Rok vydání: | 2004 |
| Předmět: |
Steric effects
chemistry.chemical_classification Epothilones Magnetic Resonance Spectroscopy Ketone Molecular Structure Spectrophotometry Infrared Stereochemistry Organic Chemistry Total synthesis Stereoisomerism Phosphonate Aldehyde Mass Spectrometry chemistry.chemical_compound chemistry Aldol condensation Lactone |
| Zdroj: | The Journal of Organic Chemistry. 69:9269-9284 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12-C13, Wadsworth-Emmons olefination of methyl ketone 28 with the phosphonate ester 8, diastereoselective aldol condensation of aldehyde 5 with the enolate of keto acid derivatives to form the C6-C7 bond, selective deprotection of acid 52, and macrolactonization. |
| Databáze: | OpenAIRE |
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