Related Experiment Video
Updated: Aug 11, 2026
08:48
Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation
Published on: January 26, 2016
Leucascandrolide a: synthesis and related studies
Alec Fettes1, Erick M Carreira
1Laboratorium für Organische Chemie, ETH Hönggerberg, Wolfgang Pauli Strasse 10, CH-8093 Zürich, Switzerland.
The Journal of Organic Chemistry
|November 25, 2003
Summary
The total synthesis of marine natural product leucascandrolide A was achieved using a convergent strategy. Key steps included diastereoselective and enantioselective reactions, leading to the macrolide moiety.
Area of Science:
- Organic Chemistry
- Natural Products Chemistry
- Synthetic Chemistry
Background:
- Leucascandrolide A is a biologically active marine natural product.
- The complex structure of leucascandrolide A presents a significant synthetic challenge.
Purpose of the Study:
- To report the first total synthesis of leucascandrolide A.
- To develop a convergent strategy for efficient macrolide assembly.
Main Methods:
- Convergent synthesis strategy.
- Diastereoselective zinc alkynilide addition to (R)-isopropylidene glyceraldehyde.
- Enantioselective copper(I) fluoride catalyzed aldol addition.
- Selenium-mediated intramolecular cyclization for tetrahydropyran formation.
- Investigation of solvent effects on macrolactonization.
Main Results:
- Successful total synthesis of leucascandrolide A.
- Efficient assembly of the macrolide core.
- Identification of critical hydrogen-bonding effects in macrolactonization.
- Development of an improved route to a key synthetic intermediate.
Conclusions:
- The developed convergent strategy enables rapid assembly of the leucascandrolide A macrolide.
- Solvent effects, particularly hydrogen-bonding, significantly influence macrolactonization.
- The synthesis provides a platform for further biological investigation of leucascandrolide A.
