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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2005
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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. |
format | Online Article Text |
id | pubmed-6147537 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2005 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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