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http://nopr.niscpr.res.in/handle/123456789/20376| Title: | One-step synthesis of 3-formyl-2-furylcarbinols and elaboration to unprecedented furotropones |
| Authors: | Dhiman, Seema Ramasastry, S S V |
| Keywords: | Furfuryl alcohols;3-Furancarboxaldehydes;3-Formyl-2-furylcarbinols;Furotropone;Cyclohepta[b]furans;Bismuth chloride;Lithiation;Alkylation;Cyclization |
| Issue Date: | 3-Aug-2013 |
| Abstract: | A general and unprecedented strategy for the synthesis of furo[2,3-d]tropone system via regioselective directed a-lithiation-alkylation and serendipitous base-promoted cyclization reaction, as key steps, has been developed. Directed a-lithiation of furan/thiophene-3-carboxaldehydes in their masked form and subsequent reaction with aldehydes efficiently provided in one-step, access to 3-formyl-2-furyl/thiophenylcarbinols, which are otherwise only accessible with difficulty. The 3-formyl-2-furylcarbinols are further elaborated to the synthesis of furo[2,3-d]tropones (also known as cyclohepta[b]furan-6-ones or furotropones) in good yields via sequential bismuth(III)chloride-catalyzed furfurylation and a novel base promoted cyclization reaction. This paper describes the general approach to the synthesis of 3-formyl-2-furylcarbinols and furotropones which could find potential applications in the synthesis of several bioactive natural products and pharmaceutics. |
| Page(s): | 1103-1112 |
| ISSN: | 0975-0975(Online); 0376-4710(Print) |
| Appears in Collections: | IJC-A Vol.52A(08-09) [August-September 2013] |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| IJCA 52A(8-9) 1103-1112_Suppl Data.pdf | Supplementary data | 1.56 MB | Adobe PDF | View/Open |
| IJCA 52A(8-9) 1103-1112.pdf | Main article | 405.45 kB | Adobe PDF | View/Open |
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