A Highly Efficient Pinacol Coupling Approach to Trehazolamine Starting from d-Glucose
| Autor: | Hansjörg Dietrich, Sofía Bobo, Storch De Gracia I, Jose Luis Chiara |
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| Jazyk: | angličtina |
| Rok vydání: | 1998 |
| Předmět: | |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname Scopus-Elsevier |
| Popis: | 7 páginas, 1 figura, 4 esquemas.-- Supporting Information Available: Experimental procedures and characterization data for compounds 16-18, and 1H NOE data for compounds 12, 13, and trans-diols A and B (3 pages) A short and very efficient synthesis of trehazolamine (3), the aglycon of the potent trehalase inhibitor trehazolin (2), has been achieved starting from d-glucose. The key transformation in this approach is a high-yielding two-step, one-pot sequence consisting of a Swern oxidation of a 1,5-diol followed by a reductive carbocyclization of the resultant 1,5-dicarbonyl compound promoted by samarium diiodide. The overall yield of 3 is 39% over nine steps from 2,3,4,6-tetra-O-benzyl-d-glucose (5). An even shorter synthesis of 30, a diastereoisomeric analogue of 3, is also described starting from 5. The key transformation in this second route is a highly stereoselective ketone oxime ether reductive carbocyclization promoted also by samarium diiodide. The overall yield of 30 is 57% over four steps from 5. This work was supported by grants PB-93-0127-C02-01 and PB-96-0833 from DGES, Ministerio de Educación y Cultura of Spain. |
| Databáze: | OpenAIRE |
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