skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Accurate stereochemistry for two related 22,26-epiminocholestene derivatives

Abstract

Regioselective opening of ring E of solasodine under various conditions afforded (25R)-22,26-epimino@@cholesta-5,22(N)-di@@ene-3β,16β-diyl diacetate (previously known as 3,16-diacetyl pseudosolasodine B), C{sub 31}H{sub 47}NO{sub 4}, or (22S,25R)-16β-hydr@@oxy-22,26-epimino@@cholesta-5-en-3β-yl acetate (a derivative of the naturally occurring alkaloid oblonginine), C{sub 29}H{sub 47}NO{sub 3}. In both cases, the reactions are carried out with retention of chirality at the C16, C20 and C25 stereogenic centers, which are found to be S, S and R, respectively. Although pseudosolasodine was synthesized 50 years ago, these accurate assignments clarify some controversial points about the actual stereochemistry for these alkaloids. This is of particular importance in the case of oblonginine, since this compound is currently under consideration for the treatment of aphasia arising from apoplexy; the present study defines a diastereoisomerically pure compound for pharmacological studies.

Authors:
; ; ; ;  [1];  [2]
  1. Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, San Manuel, 72000 Puebla, Pue. (Mexico)
  2. DEP Facultad de Ciencias Químicas, UANL, Guerrero y Progreso S/N, Col. Treviño, 64570 Monterrey, NL (Mexico)
Publication Date:
OSTI Identifier:
22347677
Resource Type:
Journal Article
Journal Name:
Acta Crystallographica. Section C, Crystal Structure Communications
Additional Journal Information:
Journal Volume: 64; Journal Issue: Pt 4; Other Information: PMCID: PMC2467522; PUBLISHER-ID: gd3197; PMID: 18391392; OAI: oai:pubmedcentral.nih.gov:2467522; Copyright (c) International Union of Crystallography 2008; This is an open-access article distributed under the terms described at http://journals.iucr.org/services/termsofuse.html.; Country of input: International Atomic Energy Agency (IAEA); Journal ID: ISSN 0108-2701
Country of Publication:
Denmark
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ACCURACY; ACETATES; ALLOCATIONS; CHIRALITY; RETENTION; RINGS

Citation Formats

Vega-Baez, José Luis, Sandoval-Ramírez, Jesús, Meza-Reyes, Socorro, Montiel-Smith, Sara, Gómez-Calvario, Victor, Bernès, Sylvain, and Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, San Manuel, 72000 Puebla, Pue. Accurate stereochemistry for two related 22,26-epiminocholestene derivatives. Denmark: N. p., 2008. Web. doi:10.1107/S0108270108005763.
Vega-Baez, José Luis, Sandoval-Ramírez, Jesús, Meza-Reyes, Socorro, Montiel-Smith, Sara, Gómez-Calvario, Victor, Bernès, Sylvain, & Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, San Manuel, 72000 Puebla, Pue. Accurate stereochemistry for two related 22,26-epiminocholestene derivatives. Denmark. https://doi.org/10.1107/S0108270108005763
Vega-Baez, José Luis, Sandoval-Ramírez, Jesús, Meza-Reyes, Socorro, Montiel-Smith, Sara, Gómez-Calvario, Victor, Bernès, Sylvain, and Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, San Manuel, 72000 Puebla, Pue. 2008. "Accurate stereochemistry for two related 22,26-epiminocholestene derivatives". Denmark. https://doi.org/10.1107/S0108270108005763.
@article{osti_22347677,
title = {Accurate stereochemistry for two related 22,26-epiminocholestene derivatives},
author = {Vega-Baez, José Luis and Sandoval-Ramírez, Jesús and Meza-Reyes, Socorro and Montiel-Smith, Sara and Gómez-Calvario, Victor and Bernès, Sylvain and Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, San Manuel, 72000 Puebla, Pue.},
abstractNote = {Regioselective opening of ring E of solasodine under various conditions afforded (25R)-22,26-epimino@@cholesta-5,22(N)-di@@ene-3β,16β-diyl diacetate (previously known as 3,16-diacetyl pseudosolasodine B), C{sub 31}H{sub 47}NO{sub 4}, or (22S,25R)-16β-hydr@@oxy-22,26-epimino@@cholesta-5-en-3β-yl acetate (a derivative of the naturally occurring alkaloid oblonginine), C{sub 29}H{sub 47}NO{sub 3}. In both cases, the reactions are carried out with retention of chirality at the C16, C20 and C25 stereogenic centers, which are found to be S, S and R, respectively. Although pseudosolasodine was synthesized 50 years ago, these accurate assignments clarify some controversial points about the actual stereochemistry for these alkaloids. This is of particular importance in the case of oblonginine, since this compound is currently under consideration for the treatment of aphasia arising from apoplexy; the present study defines a diastereoisomerically pure compound for pharmacological studies.},
doi = {10.1107/S0108270108005763},
url = {https://www.osti.gov/biblio/22347677}, journal = {Acta Crystallographica. Section C, Crystal Structure Communications},
issn = {0108-2701},
number = Pt 4,
volume = 64,
place = {Denmark},
year = {Tue Apr 01 00:00:00 EDT 2008},
month = {Tue Apr 01 00:00:00 EDT 2008}
}