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

RSC Advances Pub Date: 2019-12-05 DOI: 10.1039/C9RA09762G

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
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