Abstract
A concise synthesis of the Lycopodium alkaloid lycoposerramine Z is reported. Key to the strategy is a one-pot organocatalyzed Michael reaction followed by a domino Robinson annulation/intramolecular aza-Michael reaction promoted by LiOH, leading to enantiopure cis-decahydroquinolines.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Cyclic N-Oxides / chemical synthesis*
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Cyclic N-Oxides / chemistry
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Lycopodium / chemistry
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Molecular Structure
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Quinolines / chemical synthesis*
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Quinolines / chemistry
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Stereoisomerism
Substances
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Alkaloids
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Cyclic N-Oxides
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Quinolines
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lycoposerramine-Z
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decahydroquinoline-5-carboxylic acid