A Concise Synthesis of Siphonodictidine
| Autor: | Jean-Claude Rossier, and Adam W. Sledeski, Charles W. Jefford, John Boukouvalas, Ping-Zhong Huang |
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| Rok vydání: | 2004 |
| Předmět: |
Alkylation
Pharmaceutical Science Stereoisomerism Chemical synthesis Catalysis Analytical Chemistry Drug Discovery Animals Organic chemistry Organosilicon Compounds Furans Pharmacology Molecular Structure Chemistry Organic Chemistry Porifera Complementary and alternative medicine Yield (chemistry) ddc:540 Molecular Medicine Indicators and Reagents Sesquiterpenes Siphonodictidine |
| Zdroj: | Journal of Natural Products, Vol. 67, No 8 (2004) pp. 1383-1386 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np0400860 |
| Popis: | Siphonodictidine (1) has been synthesized for the first time in a concise and regiocontrolled manner by using 2-(tert-butyldimethylsiloxy)-3-methylfuran (6) as the crucial building block. The silver trifluoroacetate-induced alkylation of 6 with omega-bromogeranyl acetate 7 gave the key gamma-lactone intermediate 8, which on subsequent reduction, conversion of the hydroxyl into the amino group, and amidination afforded siphonodictidine (1) in an overall yield of 25.7% from 6. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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