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Total Synthesis of (-)-Gardmultimine A
Peiqi Chen1, Hesi Yang1, Hao Zhang1
1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P.R. China.
Organic Letters
|February 26, 2020
Summary
The first total synthesis of the Gardneria oxindole alkaloid (-)-gardmultimine A was achieved. This stereocontrolled synthesis utilized novel C-H borylation and cyclization methods.
Area of Science:
- Organic Chemistry
- Total Synthesis
- Medicinal Chemistry
Background:
- (-)-gardmultimine A is a complex oxindole alkaloid isolated from the Gardneria genus.
- The intricate structure of (-)-gardmultimine A presents significant synthetic challenges.
Purpose of the Study:
- To achieve the first total synthesis of (-)-gardmultimine A.
- To develop novel synthetic methodologies for constructing complex oxindole alkaloids.
Main Methods:
- A 19-step synthesis starting from d-tryptophan.
- Utilized an Iridium-catalyzed C-H borylation/oxidation for methoxyl group introduction.
- Employed a stereocontrolled oxidative rearrangement of indole to form the spirooxindole core.
- Applied an Gold(I)-catalyzed transannular Conia-ene-type cyclization for skeleton construction.
Main Results:
- Successfully synthesized (-)-gardmultimine A in a fully stereocontrolled manner.
- Established the azabicyclo[2.2.2]octane skeleton and the exocyclic E-alkene with exclusive stereoselectivity.
- Demonstrated the utility of the developed synthetic strategies for complex alkaloid synthesis.
Conclusions:
- The first total synthesis of (-)-gardmultimine A has been accomplished.
- The developed synthetic route provides a robust platform for accessing related oxindole alkaloids.
- This work expands the synthetic toolbox for complex natural product synthesis.
