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

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.

Biomimetic total synthesis of plakortone Q via acid-mediated tandem cyclization

“…Finally, tandem cyclization proceeded smoothly when 2a was treated with a catalytic amount of 10-camphorsulfonic acid (CSA) and one equivalent of H 2 O in dichloromethane. 16 Tetrahydrofuran-γ-lactone 1a was obtained in 82% yield with complete stereocontrol at the C3, C4, C5, and C6 positions. Furthermore, given the versatility of our developed tandem cyclization methodology, tetrahydrofuran-γ-lactone 1b with an opposite C8 configuration to 1a was easily prepared under similar conditions from diepoxyester 2b , which had been synthesized starting from the branched alcohol 3b (Scheme 4b).…”