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Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural Revision

Asymmetric synthesis of double bond isomers (+)-2 (Δ(15’,16’)) and (+)-3 (Δ(14’,15’)) of the structure (1) (Δ(16’,17’)) proposed for pyrinodemin A, a cytotoxic bis-pyridine alkaloid with a unique cis-cyclopent[c]isoxazolidine moiety from a marine sponge, has been accomplished. Pyrinodemin A was indi...

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Detalles Bibliográficos
Autores principales: Ishiyama, Haruaki, Tsuda, Masashi, Endo, Tadashi, Kobayashi, Jun’ichi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2005
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147537/
https://www.ncbi.nlm.nih.gov/pubmed/18007301
http://dx.doi.org/10.3390/10010312
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author Ishiyama, Haruaki
Tsuda, Masashi
Endo, Tadashi
Kobayashi, Jun’ichi
author_facet Ishiyama, Haruaki
Tsuda, Masashi
Endo, Tadashi
Kobayashi, Jun’ichi
author_sort Ishiyama, Haruaki
collection PubMed
description Asymmetric synthesis of double bond isomers (+)-2 (Δ(15’,16’)) and (+)-3 (Δ(14’,15’)) of the structure (1) (Δ(16’,17’)) proposed for pyrinodemin A, a cytotoxic bis-pyridine alkaloid with a unique cis-cyclopent[c]isoxazolidine moiety from a marine sponge, has been accomplished. Pyrinodemin A was indicated to be a 1:1 racemic mixture of 2 from comparison of C(18) and chiral HPLC analysis for pyrinodemin A and the synthetic compounds as well as ESIMS data of oxidative degradation products of pyrinodemin A.
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spelling pubmed-61475372018-11-19 Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural Revision Ishiyama, Haruaki Tsuda, Masashi Endo, Tadashi Kobayashi, Jun’ichi Molecules Article Asymmetric synthesis of double bond isomers (+)-2 (Δ(15’,16’)) and (+)-3 (Δ(14’,15’)) of the structure (1) (Δ(16’,17’)) proposed for pyrinodemin A, a cytotoxic bis-pyridine alkaloid with a unique cis-cyclopent[c]isoxazolidine moiety from a marine sponge, has been accomplished. Pyrinodemin A was indicated to be a 1:1 racemic mixture of 2 from comparison of C(18) and chiral HPLC analysis for pyrinodemin A and the synthetic compounds as well as ESIMS data of oxidative degradation products of pyrinodemin A. MDPI 2005-01-31 /pmc/articles/PMC6147537/ /pubmed/18007301 http://dx.doi.org/10.3390/10010312 Text en © 2005 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.
spellingShingle Article
Ishiyama, Haruaki
Tsuda, Masashi
Endo, Tadashi
Kobayashi, Jun’ichi
Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural Revision
title Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural Revision
title_full Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural Revision
title_fullStr Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural Revision
title_full_unstemmed Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural Revision
title_short Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural Revision
title_sort asymmetric synthesis of double bond isomers of the structure proposed for pyrinodemin a and indication of its structural revision
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147537/
https://www.ncbi.nlm.nih.gov/pubmed/18007301
http://dx.doi.org/10.3390/10010312
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