Issue 69, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
25 Oct 2019
Accepted
26 Nov 2019
First published
05 Dec 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 40368-40377

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

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