Schumacher, Andreas and Jessen, Henning J. and Schmid, Fabian and Pfaltz, Andreas and Gademann, Karl. (2011) Catalytic Enantioselective Total Synthesis of (+)-Torrubiellone. Organic Letters, 13 (16). pp. 4368-4370.
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Official URL: http://edoc.unibas.ch/dok/A5849083
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Abstract
Silyl-protected (R)-methyl 2-(hydroxymethyl)butanoate was obtained by an enantioselective Ir-catalyzed hydrogenation in high yield and selectivity. Elaboration of this building block via Takai and Stille reactions gave a protected hydroxy polyene chain, which was coupled to a 5-hydroxyphenyl-4-hydroxy-2-pyridone derivative by a modified Horner-Wadsworth-Emmons reaction. Deprotection gave synthetic (+)-torrubiellone C, which led to the assignment of the configuration of the natural product as (R).
| Faculties and Departments: | 05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Organische Chemie (Gademann) 05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Synthetische organische Chemie (Pfaltz) |
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| UniBasel Contributors: | Gademann, Karl and Pfaltz, Andreas |
| Item Type: | Article, refereed |
| Article Subtype: | Research Article |
| Publisher: | American Chemical Society |
| ISSN: | 1523-7060 |
| e-ISSN: | 1523-7052 |
| Note: | Publication type according to Uni Basel Research Database: Journal article |
| Identification Number: |
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| Last Modified: | 10 Apr 2017 09:49 |
| Deposited On: | 14 Sep 2012 07:02 |
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