Jump to main content
Jump to site search

Issue 69, 2019
Previous Article Next Article

Total synthesis of squafosacin F: stereodivergent approach to mono-tetrahydrofuran acetogenins

Author affiliations

Abstract

Annonaceous acetogenins have a wide range of potential biological activities. The development of simple and diversity-oriented approaches to their synthesis is therefore important. We have achieved the first total synthesis of squafosacin F and assigned its absolute configuration. The key steps were an acid-mediated tandem intramolecular double cyclization to build the hydroxy-flanked mono-tetrahydrofuran core and decoration with the desired functionalities of the target natural product via highly stereoselective reactions.

Graphical abstract: Total synthesis of squafosacin F: stereodivergent approach to mono-tetrahydrofuran acetogenins

Back to tab navigation

Supplementary files

Article information


Submitted
25 Oct 2019
Accepted
26 Nov 2019
First published
05 Dec 2019

This article is Open Access

RSC Adv., 2019,9, 40368-40377
Article type
Paper

Total synthesis of squafosacin F: stereodivergent approach to mono-tetrahydrofuran acetogenins

K. Ota, S. Kohno, T. Yamashita, A. Miura, K. Kamaike and H. Miyaoka, RSC Adv., 2019, 9, 40368
DOI: 10.1039/C9RA09762G

This article is licensed under a Creative Commons Attribution-NonCommercial 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 and it is not used for commercial purposes.

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.


Social activity

Search articles by author

Spotlight

Advertisements