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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
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Trichormamide C Structural Confirmation through Total Synthesis and Extension to Analogs
Laurine Darcel1, Mahamadou Djibo1, Michel Gaillard1
1PSL Université Paris: EPHE-UPVD-CNRS, USR 3278 CRIOBE , Université de Perpignan Via Domitia, 58 avenue Paul Alduy , 66860 Perpignan , France.
Organic Letters
|December 20, 2019
Summary
Marine natural products are key for drug discovery. Total synthesis confirmed the structure of Trichormamide C, a cyclic lipopeptide from cyanobacteria, leading to new analogs.
Area of Science:
- Marine natural products chemistry
- Organic synthesis
- Drug discovery
Background:
- Marine natural products are a promising source for novel therapeutics.
- Cyanobacteria, such as *Oscillatoria* sp., produce complex bioactive compounds.
- Trichormamide C is a cyclic lipopeptide containing nonproteinogenic amino acids.
Purpose of the Study:
- To confirm the structure of Trichormamide C through total synthesis.
- To develop a flexible synthetic route for Trichormamide C and its analogs.
- To explore structure-activity relationships of Trichormamide C.
Main Methods:
- Total synthesis of Trichormamide C.
- Development of a flexible synthetic strategy.
- Isolation and characterization of novel analogs.
Main Results:
- Successful total synthesis of Trichormamide C (1).
- Generation of two new Trichormamide C analogs (3 and 4) via flexible synthesis.
- Confirmation of the cyclic lipopeptide structure.
Conclusions:
- Total synthesis is crucial for validating marine natural product structures.
- The developed synthetic route allows for the creation of Trichormamide C analogs.
- This work contributes to the understanding of marine-derived cyclic lipopeptides for potential pharmaceutical applications.
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