Catalytic Enantioselective Total Synthesis of (+)-Torrubiellone

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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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 > Chemie > Synthetische organische Chemie (Pfaltz)
UniBasel Contributors:Gademann, Karl and Pfaltz, Andreas
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:10 Apr 2017 09:49
Deposited On:14 Sep 2012 07:02

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