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Synthesis of Furans

By: William Sommer, Aldrich ChemFiles 2009,9.6, 5.

Aldrich ChemFiles 2009, 9.6, 5.

Donohoe and co-workers have developed several synthetic approaches to the synthesis of furans which incorporate RCM as a key step.1 In 2007, the researchers synthesized a series of di- and tri-substituted furans using both the Hoveyda-Grubbs catalyst (2nd Generation) and the Grubbs catalyst (2nd Generation), followed by addition of PPTS or TFA, respectively (Scheme 7).

Scheme 7

In 2008, Donohoe and coworkers devised a synthesis of (–)‑ (Z)-deoxypukalide, a member in a class of marine natural products which have exhibited a range of biological activities, including neurotoxicity and anti-inflammatory effects. In the total synthesis of (–)-( Z)-deoxypukalide, mixed acetal formation with acrolein diethyl acetal served to install the requisite allyl group and following RCM, acidic hydrolysis furnished the desired furan in good overall yield. The final step of the synthesis utilized a second RCM with the Grubbs catalyst (2nd Generation) to form the butenolide unit in 72% yield (Scheme 8).2

Scheme 8

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Materials

     

References

  1. (a) Donohoe, T. J. et al. Eur. J. Org. Chem. 2005, 1969. (b) Donohoe, T. J. et al. Tetrahedron 2008, 64, 809. (c) Donohoe, T. J. et al. Org. Lett. 2006, 8, 543. (d) Donohoe, T. J. et al. Chem. Eur. J. 2008, 14, 5716.
  2. Donohoe,T. J. et al. Angew. Chem. Int. Ed. 2008, 47, 7314.

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