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How thiostrepton was made in the laboratory.
1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA. kcn@scripps.edu
Angewandte Chemie (International Ed. in English)
|December 5, 2012
Summary
The total synthesis of the thiopeptide antibiotic thiostrepton was achieved in 2004. This review details the challenging, multi-step laboratory journey to its successful creation.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Chemical Synthesis
Background:
- Thiostrepton is a potent thiopeptide antibiotic.
- The laboratory synthesis of thiostrepton was a significant challenge.
- Previous synthetic routes were not established before 2004.
Purpose of the Study:
- To provide a comprehensive review of the first total laboratory synthesis of thiostrepton.
- To detail the novel strategies and tactics employed in the synthesis.
- To recount the challenges and lessons learned during the synthetic campaign.
Main Methods:
- Retrosynthetic analysis of the complex thiopeptide structure.
- Development of innovative synthetic methodologies for key fragments.
- Stepwise assembly and finalization of the thiostrepton molecule.
Main Results:
- Successful completion of the first total synthesis of thiostrepton in 2004.
- Elucidation of novel chemical reactions and strategies applicable to thiopeptide synthesis.
- Overcoming significant synthetic roadblocks through creative problem-solving.
Conclusions:
- The total synthesis of thiostrepton represents a landmark achievement in organic synthesis.
- The synthetic journey provided valuable insights into thiopeptide chemistry.
- The developed strategies offer a blueprint for the synthesis of other complex natural products.
