A Versatile Approach for the Total Syntheses of Fuscinarin and Fuscins

Abstract

The first total synthesis of fuscinarin (1) and total synthesis of fuscins, the pentaketide metabolites showing activity against CCR5 in a scintillation proximity assay, were described by using compound 6 as a common intermediate. A key feature of the approach is the microwave-assisted tandem ortho-Claisen/Cope rearrangement that was used for the expedient synthesis of the intermediate 10.

Isomerization of Allylbenzenes

“…A sodium hydroxide-catalyzed isomerization of allylbenzene 105 under PTC was used as one key synthetic step during the total synthesis of fuscinarin by Xie and co-workers . The researchers used sodium hydroxide with TBAB to isomerize the allyl group in 105 , to afford 106 in an excellent yield of 96%.…”

“…A sodium hydroxide-catalyzed isomerization of allylbenzene 105 under PTC was used as one key synthetic step during the total synthesis of fuscinarin by Xie and co-workers. 249 The researchers used sodium hydroxide with TBAB to isomerize the allyl group in 105, to afford 106 in an excellent yield of 96%. Reduction of the ketone, followed by ozonolytic cleavage of the 1-propenyl group, then afforded the hemiacetal 107, which was readily converted into fuscinarin 108 over two steps as shown in Scheme 24.…”

Enantioselective Allylation of Oxocarbenium Ions Catalyzed by Bi(OAc)3/Chiral Phosphoric Acid

“…Phthalides, especially optically active 3-substituted isobenzofuranones bearing trisubstituted stereocenters, are found extensively in natural products and bioactive compounds (Scheme ). For instance, as an effective human CCR5 antagonist, Fuscinarin can block the entry of HIV virus . (−)-Herbaric acid was used as an antibacterial reagent .…”

Highly efficient and enantioselective synthesis of chiral lactones via Ir-catalysed asymmetric hydrogenation of ketoesters

“…3 Fuscinarin is an effective human CCR5 antagonist and it can defend against HIV virus. 4 (−)-Herbaric acid is used as an antibacterial reagent. 5 (+)-Harzialactone A has anti-leishmanial effects.…”