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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Total synthesis of (-)-lycoperine A
Yoshitaka Nakamura1, Anthony M Burke, Shunsuke Kotani
1Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
Organic Letters
|December 2, 2009
Summary
Researchers synthesized Lycoperine A using a convergent route, achieving the complex molecule in 13 steps. This study details the synthetic pathway and confirms the absolute configuration of Lycoperine A.
Area of Science:
- Organic Synthesis
- Total Synthesis
- Medicinal Chemistry
Background:
- Lycoperine A is a complex natural product with potential biological activity.
- Efficient synthetic routes are crucial for studying and developing natural products.
Purpose of the Study:
- To develop a highly convergent synthetic route for Lycoperine A.
- To establish the absolute configuration of Lycoperine A.
Main Methods:
- Convergent synthesis involving double alkylation of a piperidine derivative with an octahydroquinoline moiety.
- Desymmetrization of 5-methylcyclohexane-1,3-dione to prepare the octahydroquinoline intermediate.
- Multi-step sequence including hydrolysis, reductive amination, and cyclization.
Main Results:
- Successful synthesis of the Lycoperine A skeleton.
- Lycoperine A was obtained in 13 steps with a 3% overall yield.
- The absolute configuration was assigned as 6R,6'R,8R,8'R,13S,17R.
Conclusions:
- A practical and efficient synthetic strategy for Lycoperine A was established.
- The synthesis provides access to Lycoperine A for further biological evaluation.
- The stereochemical assignment is confirmed through synthesis.
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