Total Synthesis of 7-epi-Pukalide and 7-Acetylsinumaximol B

Abstract

Convergent total syntheses of the furanocembranoids 7-epi-pukalide and 7-acetylsinumaximol B have been achieved using a one-pot Knoevenagel condensation and thioether-mediated furan-forming reaction. Furan formation proceeds via a sulfur ylide and results in rapid introduction of structural complexity during the coupling of two highly functionalised fragments. The targets have been prepared in 16 steps from (R)-perillyl alcohol.

Keywords: cembrane; lactonisation; natural products; ring-closing metathesis; total synthesis.