Synthesis of Lycopodium alkaloids. II. Development of stereospecific synthetic methods.
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[reaction: see text] A strategy for the synthesis of the spirocyclic core of spirolucidine was explored through a model study. The diene 4a was prepared and photolyzed to give the desired [2 + 2] photoadduct 17 containing the correct relative stereochemistry corresponding to spirolucidine.
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Phlegmariurine B (1), a known alkaloid, along with three new analogous compounds, 2alpha-hydroxyphlegmariurine B (2), 2-oxoyphlegmariurine B (3) and 11-oxophlegmariurine B (4), were isolated from the CHCl3 fraction of total alkaloids of whole plant of the Chinese medicinal herb Huperzia serrata. Their structures were elucidated by spectral analysis.
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