A Concise Route to Branched Erythrono-γ-lactones. Synthesis of the Leaf-Closing Substance Potassium (±)-(2R,3R)-2,3,4-Trihydroxy-2-methylbutanoate
| Autor: | Tony V. Robinson, Daniel Sejer Pedersen, Edward R. T. Tiekink, D. K. Taylor |
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| Rok vydání: | 2009 |
| Předmět: |
chemistry.chemical_classification
Biological Products Potassium hydroxide Lactol Potassium Organic Chemistry Sugar Acids chemistry.chemical_element Plants Chemical synthesis Dioxanes Plant Leaves Butyric acid Lactones chemistry.chemical_compound chemistry Yield (chemistry) Structural isomer Organic chemistry Lactone |
| Zdroj: | The Journal of Organic Chemistry. 74:4400-4403 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo900392y |
| Popis: | A series of 1,2-dioxanes 3 were ring-opened with Co(SALEN)(2) to furnish lactol regioisomers 4 and 5 (86-99% yield). The lactols were oxidized to gamma-lactones 8 and 9 (72-96% yield) and deprotected to afford the 2-C- and 3-C-alkyl and aryl branched erythrono-gamma-lactones 1, 6, and 7 (65-94% yield), including the natural plant lactone (+/-)-2-C-d-methylerythrono-1,4-lactone 1. The latter compound was treated with aqueous potassium hydroxide to afford potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate 2, which is a leaf-closing substance of Leucaena leucocephalam. |
| Databáze: | OpenAIRE |
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