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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Total synthesis of brevisamide
1Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Organic Letters
|September 10, 2009
Summary
A new convergent synthesis of brevisamide was achieved using a crotyl silane-based [4 + 2]-annulation. This method efficiently prepared an oxygenated tetrahydropyran intermediate and a conjugated diene side chain.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Brevisamide is a complex natural product with potential biological activity.
- Efficient synthetic routes are crucial for accessing and studying such molecules.
Purpose of the Study:
- To develop a novel and convergent synthetic strategy for brevisamide.
- To establish a robust method for constructing key intermediates.
Main Methods:
- Utilized a crotyl silane-based [4 + 2]-annulation reaction.
- Employed modified Negishi cross-coupling for side chain construction.
Main Results:
- Successfully synthesized an advanced oxygenated tetrahydropyran intermediate.
- Efficiently constructed the conjugated (E,E)-diene side chain.
Conclusions:
- The described convergent synthesis provides an effective route to brevisamide.
- The employed annulation and cross-coupling methods are valuable for complex molecule synthesis.
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