Total synthesis of squafosacin F: stereodivergent approach to mono-tetrahydrofuran acetogenins. Issue 69 (5th December 2019)

• Record Type: Journal Article
• Authors: Ota, Koichiro; Kohno, Sumika; Yamashita, Tomoko; Miura, Atsuko; Kamaike, Kazuo; Miyaoka, Hiroaki
• Is Part Of: RSC advances. Volume 9:Issue 69(2019)
• Page Start: 40368
• Page End: 40377
• Publication Date: 2019-12-05
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9ra09762g
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : The first total synthesis of squafosacin F was achieved via construction of the hydroxy-flanked mono-tetrahydrofuran by acid-mediated tandem cyclization as a key step. 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.