Synthesis of the AD ring biaryl ether 7. DMF=N,N-dime- thylformamide, PPTS=pyridinium p-toluenesulfonate

March 06, 2024

• Title:       

  Synthesis of the AD ring biaryl ether 7. DMF=N,N-dime- thylformamide, PPTS=pyridinium p-toluenesulfonate

• Image Source:

  Total synthesis of cavicularin and riccardin C: Addressing the synthesis of an arene that adopts a boat configuration

• Mark:

  Scheme 2

• Associated context:

  Our synthesis began with the protection of isovanillin as its dioxolane acetal 4. Union of 4 with 4-fluorobenzaldehyde then gave diaryl ether 5, which was reduced with sodium borohydride to the corresponding alcohol. Bromination with CBr₄/PPh₃ additionally unmasked the latent aldehyde function to give 6, which, on sequential treatment with PPh₃ and neopentyl glycol, led to the suitably functionalized AD ring system 7 (Scheme 2)