3 years ago

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

Total Synthesis of 7-epi-Pukalide and 7-Acetylsinumaximol B
Kirsten McAulay, J. Stephen Clark
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. Inspired by nature: The furanocembranoids 7-epi-pukalide and 7-acetyl-sinumaximol B have been synthesised by a convergent route in which a one-pot Knoevenagel condensation and tetrahydrothiophene-mediated furan-forming reaction is used to couple two fragments to give the complete carbon framework.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702591

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