Isolation, identification and determination of the absolute configuration of Fischerellin B. A new algicide from the freshwater cyanobacterium Fischerella muscicola (Thuret)

A new 2-pyrrolidinone with a polyunsaturated side chain has been identified from the cyanobacterium Fischerella muscicola (Thuret). Its structure was elucidated by UV, NMR and mass spectroscopy. Derivatisation of the natural product and stereocontrolled synthesis of the derivative allowed the determ...

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Bibliographic Details
Published inTetrahedron letters Vol. 38; no. 3; pp. 379 - 382
Main Authors Papke, Ulrich, Gross, Elisabeth M., Francke, Wittko
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:A new 2-pyrrolidinone with a polyunsaturated side chain has been identified from the cyanobacterium Fischerella muscicola (Thuret). Its structure was elucidated by UV, NMR and mass spectroscopy. Derivatisation of the natural product and stereocontrolled synthesis of the derivative allowed the determination of the absolute configuration by means of chiral gas chromatography. The new compound, fischerellin B, shows algicidal properties. By means of spectroscopic methods, microreactions and partial synthesis, the structure of fischerellin B was determined to be (3 R,5 S)-3-methyl-5-((5 E)-pentadec-5-ene-7,9-diynyl)-pyrrolidin-2-one.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(96)02284-8