Jump to main content
Jump to site search

Issue 2, 2017
Previous Article Next Article

Cycloelatanene A and B: absolute configuration determination and structural revision by the crystalline sponge method

Author affiliations

Abstract

Cycloelatanene A and B are marine natural products first reported a few years ago. Their relative structures had been elucidated by an extensive NMR study and found to be epimers. However, their absolute configurations had not been established because they were isolated in only minute quantities as oily compounds. In this study, the complete structures of cycloelatanene A and B, including absolute configurations, were determined by the crystalline sponge method. The structure analysis confirmed the unique tricyclic structure involving a spiro[5.5]undecene skeleton. One stereogenic centre at C4 was revised as a result of this analysis. Since it only took 1–2 weeks to complete the experiments using the crystalline sponge method (guest-soaking followed by crystallographic analysis), this method is now highly recommended as a first port of call to achieve complete natural product structure elucidation.

Graphical abstract: Cycloelatanene A and B: absolute configuration determination and structural revision by the crystalline sponge method

Back to tab navigation

Supplementary files

Publication details

The article was received on 26 Sep 2016, accepted on 26 Oct 2016 and first published on 27 Oct 2016


Article type: Edge Article
DOI: 10.1039/C6SC04288K
Citation: Chem. Sci., 2017,8, 1547-1550
  • Open access: Creative Commons BY license
  •   Request permissions

    Cycloelatanene A and B: absolute configuration determination and structural revision by the crystalline sponge method

    S. Lee, M. Hoshino, M. Fujita and S. Urban, Chem. Sci., 2017, 8, 1547
    DOI: 10.1039/C6SC04288K

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements