Abstract
The pentacyclic alkaloid (±)-meloscine was prepared in 19 steps through a reaction sequence that features a putative azatrimethylenemethane intermediate, generated through cascade cyclization of an allenyl azide substrate, to deliver the core azabicyclo[3.3.0]octadiene substructure. Subsequent manipulation of the peripheral functionality then delivered (±)-meloscine.
© 2012 American Chemical Society
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Azides / chemistry*
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Cyclization
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Models, Molecular
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Molecular Structure
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Polycyclic Compounds / chemical synthesis*
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Quinolines / chemical synthesis*
Substances
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Azides
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Bridged Bicyclo Compounds, Heterocyclic
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Polycyclic Compounds
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Quinolines
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meloscine