Structure Characterization, Biomimetic Total Synthesis, and Optical Purity of Two New Pyrrolidine Alkaloids, Pandamarilactonine-A and -B, Isolated from Pandanus amaryllifolius Roxb

Two new alkaloids, both possessing a pyrrolidinyl α,β-unsaturated γ-lactone residue and a γ-alkylidene α,β-unsaturated γ-lactone residue, were isolated from a tropical medicinal plant, Pandanus amaryllifolius Roxb. Their structures were deduced by spectroscopic analysis including the new NMR techniq...

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Veröffentlicht in:Journal of the American Chemical Society 2000-09, Vol.122 (36), p.8635-8639
Hauptverfasser: Takayama, Hiromitsu, Ichikawa, Tomotake, Kuwajima, Toshiyuki, Kitajima, Mariko, Seki, Hiroko, Aimi, Norio, Nonato, Maribel G
Format: Artikel
Sprache:eng
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Zusammenfassung:Two new alkaloids, both possessing a pyrrolidinyl α,β-unsaturated γ-lactone residue and a γ-alkylidene α,β-unsaturated γ-lactone residue, were isolated from a tropical medicinal plant, Pandanus amaryllifolius Roxb. Their structures were deduced by spectroscopic analysis including the new NMR technique PFG J-HMBC 2D spectroscopy and then confirmed by biomimetic total synthesis. It was found that one diastereoisomer, pandamarilactonine-A (1), comprised a mixture enriched with (+)-enantiomer, while another diastereomeric isomer, pandamarilactonine-B (2), occurred as a racemate.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0009929