Regio- and Stereocontrolled Dieckmann Approach to Treprostinil-Inspired, Polycyclic Scaffold For Building Macrocyclic
Srinivas Chamakuri1, Srinvas Jogula1, Prabhat Arya1
1Dr. Reddy's Institute of Life Sciences (DRILS), University of Hyderabad Campus Gachibowli, 500046, Hyderabad, India.
Researchers created a new synthetic method for natural product-like compounds inspired by treprostinil (UT-15). This approach enables the synthesis of diverse macrocyclic compounds with potential for exploring chiral side chains.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Synthetic Chemistry
Background:
- Development of a novel synthetic strategy utilizing regio- and stereocontrolled Dieckmann cyclization.
- Inspiration drawn from the treprostinil (UT-15) structure for scaffold design.
Discussion:
- Application of the developed method for the synthesis of 15-membered macrocyclic hybrid compounds.
- Incorporation of an amino acid moiety within the macrocyclic skeleton to facilitate structural diversity.
Key Insights:
- Successful regio- and stereoselective synthesis of a complex natural-product-like scaffold.
- Demonstration of a diversity-based approach for generating novel macrocyclic structures.
- Establishment of a platform for exploring various chiral side chain modifications.
Outlook:
- Potential for the synthesized compounds in drug discovery and development.
- Further exploration of the biological activities of these novel macrocyclic hybrids.
- Expansion of the synthetic methodology to access a wider range of complex molecules.
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: Overview
Woodward–Hoffmann Selection Rules and Microscopic Reversibility
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

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