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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.

SUBMITTER: Ota K

PROVIDER: S-EPMC9076243 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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

Ota Koichiro K Kohno Sumika S Yamashita Tomoko T Miura Atsuko A Kamaike Kazuo K Miyaoka Hiroaki H

RSC advances 20191205 69

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 <i>via</ ...[more]

PMID: 35542676

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