Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus)

Angela Nelson, H. Martin Garraffo, Thomas F. Spande, John W. Daly, Paul J. Stevenson

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Abstract

A short synthesis of the postulated structure for indolizidine alkaloid 259B with the hydrogens at C5 and C9 entgegen has been achieved with complete control of stereochemistry at C5. Both diastereoisomers at C8 were obtained, but neither proved to be the natural product. The comparison of the mass and FTIR spectral properties of the synthetic compounds to those of the natural material strongly suggest that the gross structure is correct and that the difference may be a branch in the C5 alkyl side-chain. The GC-retention times of the two synthetic compounds were markedly longer than that of the natural 5,9E-259B.
Original languageEnglish
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Volume4
Issue number6
DOIs
Publication statusPublished - 21 Jan 2008

ASJC Scopus subject areas

  • Organic Chemistry

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