Two Total Syntheses of Trigoxyphins K and L.
Shuyang Li1, Jack A O'Hanlon1, Andrew Mattimoe1
1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom.
Organic Letters
|October 6, 2023
Summary
Researchers achieved two total syntheses of trigoxyphins K and L, complex tricyclic terpenoids. These novel synthetic routes provide access to these natural products from Trigonostemon xyphophylloides.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Trigoxyphins K and L are tricyclic terpenoids isolated from Trigonostemon xyphophylloides.
- Natural products often possess unique structural features and biological activities.
Purpose of the Study:
- To develop and present two distinct total syntheses for trigoxyphins K and L.
- To explore novel synthetic strategies for complex terpenoid structures.
Main Methods:
- Electrophilic cyclization of A/C-ring substrates followed by 1O2-mediated hydroxybutenolide formation and Luche reduction.
- Tetralone ring expansion followed by O-demethylation-lactonization-isomerization and enolate oxygenation.
Main Results:
- Successful synthesis of trigoxyphin L via electrophilic cyclization and subsequent synthesis of trigoxyphin K.
- Efficient synthesis of trigoxyphin K from a tetralone intermediate, followed by trigoxyphin L.
Conclusions:
- Two viable and distinct synthetic pathways to trigoxyphins K and L have been established.
- These syntheses demonstrate the feasibility of constructing complex tricyclic terpenoid frameworks.
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