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Total Synthesis of (-)-Exiguolide
Zhigao Zhang1, Hengmu Xie1, Hongze Li1
1Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, ‡State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, P. R. China.
Organic Letters
|September 16, 2015
Summary
Researchers achieved a concise total synthesis of (-)-exiguolide, a complex molecule, using 20 steps. Key strategies included Prins cyclization for A ring construction and a novel side chain installation for macrocyclization.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- (-)-Exiguolide is a natural product with potential biological significance.
- Total synthesis provides access to complex molecules for further study.
Purpose of the Study:
- To develop a concise and efficient total synthesis of (-)-exiguolide.
- To explore novel synthetic strategies for complex natural product assembly.
Main Methods:
- Prins cyclization and homobromination for A ring construction.
- Sonogashira cross-coupling and ring-closing metathesis for side chain installation and macrocyclization.
Main Results:
- Successful total synthesis of (-)-exiguolide in 20 steps.
- Achieved excellent cis-Z stereochemical control during A ring formation.
- Demonstrated an efficient macrocyclization strategy.
Conclusions:
- The developed synthetic route is concise and effective for accessing (-)-exiguolide.
- The employed strategies offer valuable insights for the synthesis of related complex molecules.
