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Total synthesis of laidlomycin
Wonchul Lee1, Sungkyoung Kang, Byunghyuck Jung
1MIRC, Department of Chemistry, KAIST, Daejeon 34141, Korea. hee-seung_lee@kaist.ac.kr shkang@kaist.ac.kr.
Chemical Communications (Cambridge, England)
|February 5, 2016
Summary
This study details the total synthesis of laidlomycin, a complex natural product. Key steps include stereocontrolled coupling, spiroketalization, and various asymmetric transformations to build the molecule.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Asymmetric Synthesis
Background:
- Laidlomycin is a polyether ionophore antibiotic with complex stereochemistry.
- Total synthesis of complex natural products presents significant challenges in stereocontrol and efficiency.
Purpose of the Study:
- To achieve the total synthesis of laidlomycin.
- To develop and apply novel synthetic strategies for constructing complex stereocenters.
Main Methods:
- Stereocontrolled synthesis of a key aldehyde intermediate.
- Coupling of a β-keto phosphonate with the aldehyde.
- Sequential hydrogenolysis/hydrogenation and equilibration for spiroketalization.
- Application of various asymmetric reactions including desymmetrization, allylation, epoxidation, reduction, and alkylation.
Main Results:
- Successful synthesis of laidlomycin.
- Establishment of a stereocontrolled route to key intermediates.
- Efficient construction of multiple stereocenters using diverse synthetic methodologies.
- Demonstration of thermodynamic control for spiroketal formation.
Conclusions:
- The total synthesis of laidlomycin was accomplished.
- The developed synthetic route is efficient and stereoselective.
- This work provides a valuable blueprint for the synthesis of related complex natural products.