Journal
ORGANIC LETTERS
Volume 12, Issue 1, Pages 72-75Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol902389e
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Funding
- Schering-Plough Research Institute
- S. T. Li foundation
- Daiichi-Sankyo
- Japan Society for the Promotion of Science
- NATIONAL CENTER FOR RESEARCH RESOURCES [S10RR017915] Funding Source: NIH RePORTER
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Lycoperine A was synthesized through a highly convergent route in which a double alkylation of 2,6-dicyano-N-benzylpiperidine with the octahydroquinoline moiety gave the lycoperine skeleton. The octahydroquinoline was prepared by a desymmetrization reaction of 5-methylcyclohexane-1,3-dione. Hydrolysis, reductive amination, and cyclization gave lycoperine A in 13 steps and 3% overall yield. The absolute configuration of lycoperine A was assigned as 6R,6'R,8R,8'R,13S,17R.
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