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Structure-Elucidating Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone C§

Drescher, Christian and Keller, Morris and Potterat, Olivier and Hamburger, Matthias and Brückner, Reinhard. (2020) Structure-Elucidating Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone C§. Organic Letters, 22 (7). pp. 2559-2563.

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Official URL: https://edoc.unibas.ch/78654/

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Abstract

The (polyenoyl)tetramic acid militarinone C (1) heads a family of seven members. Before our work, the configuration of C-5 was unknown whereas the configurations of C-8′ and C-10′ were either (R,R) or (S,S). We synthesized the four stereoisomers of constitution 1, which conform with these insights. This included cross-coupling both enantiomers of the western building block (8) with both enantiomers of the eastern building block (9). The specific rotations of the resulting 1 isomers suggested that natural 1 is configured like the coupling partners (S)-8 and (R,R)-9. This conclusion was corroborated by degrading natural 1 to alcohol 35 and by proving its configurational identity with synthetic (R,R)-35.
Faculties and Departments:05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Pharmazie > Pharmazeutische Biologie (Hamburger)
UniBasel Contributors:Hamburger, Matthias and Keller, Morris and Potterat, Olivier
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:
Last Modified:01 Nov 2021 16:42
Deposited On:01 Nov 2021 16:42

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