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

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...

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Autores principales: Nelson, Angela, Garraffo, H Martin, Spande, Thomas F, Daly, John W, Stevenson, Paul J
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2008
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2244622/
https://www.ncbi.nlm.nih.gov/pubmed/18208586
http://dx.doi.org/10.1186/1860-5397-4-6
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author Nelson, Angela
Garraffo, H Martin
Spande, Thomas F
Daly, John W
Stevenson, Paul J
author_facet Nelson, Angela
Garraffo, H Martin
Spande, Thomas F
Daly, John W
Stevenson, Paul J
author_sort Nelson, Angela
collection PubMed
description 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.
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spelling pubmed-22446222008-02-15 Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus) Nelson, Angela Garraffo, H Martin Spande, Thomas F Daly, John W Stevenson, Paul J Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2008-01-21 /pmc/articles/PMC2244622/ /pubmed/18208586 http://dx.doi.org/10.1186/1860-5397-4-6 Text en Copyright © 2008, Nelson et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Nelson, Angela
Garraffo, H Martin
Spande, Thomas F
Daly, John W
Stevenson, Paul J
Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus)
title Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus)
title_full Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus)
title_fullStr Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus)
title_full_unstemmed Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus)
title_short Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus)
title_sort facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9e-259b from a bufonid toad (melanophryniscus)
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2244622/
https://www.ncbi.nlm.nih.gov/pubmed/18208586
http://dx.doi.org/10.1186/1860-5397-4-6
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