An Alternative Synthetic Route to (3R,5S,1′S)-5-{1′-[(tert-Butyloxycarbonyl)amino]-3′-methylbutyl}-3-methyldihydrofuran-2(3H)-one, a Precursor of a Leu-Ala Hydroxyethylene Isostere
| Autor: | M. Rita Ventura, Olga Iranzo, Helder Vila-Real, Ana Luísa Simplício, Christopher D. Maycock |
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| Rok vydání: | 2015 |
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| Zdroj: | Synthesis. 47:3009-3012 |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/s-0034-1381036 |
| Popis: | An improved synthetic route to (3R,5S,1′S)-5-{1′-[(tert-butyloxycarbonyl)amino]-3′-methylbutyl}-3-methyldihydrofuran-2(3H)-one, a lactone precursor of the Leu-Ala (2R,4S,5S) hydroxyethylene isostere found in many peptidomimetic aspartyl protease inhibitors of Alzheimer’s disease, is devised. Alkylation of N-Boc-leucinal with the lithium salt of benzyl propargyl ether instead of ethyl propiolate is the key toward a more reproducible and efficient route to obtain the title lactone from N-Boc- l -leucine in six steps, and an overall yield of 16%. |
| Databáze: | OpenAIRE |
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