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

Beilstein Journal of Organic Chemistry
Angela NelsonPaul J Stevenson

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.

References

Oct 24, 2001·The Journal of Organic Chemistry·Daniel L. CominsLawrence A. Morgan
May 24, 2003·The Journal of Organic Chemistry·Joel M Harris, Albert Padwa
Jul 16, 2005·Organic Letters·Amos B Smith, Dae-Shik Kim
Oct 29, 2005·Journal of Natural Products·John W DalyH Martin Garraffo
Feb 3, 2007·Natural Product Reports·Joseph P Michael
Apr 14, 2007·Clinics in Podiatric Medicine and Surgery·Aileen M Takahashi
Mar 12, 2011·The Journal of Antimicrobial Chemotherapy·Jae-Hoon SongUNKNOWN ANSORP Study Group

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Citations

Oct 14, 2008·Toxicon : Official Journal of the International Society on Toxinology·John W DalyJulián Faivovich

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Methods Mentioned

BETA
NMR

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