Topic
Ferrier carbocyclization
About: Ferrier carbocyclization is a research topic. Over the lifetime, 66 publications have been published within this topic receiving 947 citations.
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TL;DR: 2-C- and 3-C-[(2'-chloro)pyrid-5'-yl]-hex-5-enopyranosides were synthesized from 4,6-O-benzylidene acetals in three steps by treatment with mercury or palladium salts and the corresponding cyclohexanones could be obtained.
5 citations
TL;DR: Cyclophellitol and its C3-epimer have been synthesized from 5-enoglucopyranoside and5-enomannopyranuside, respectively, using a Ferrier-II reaction meditated by PdCl2.
Abstract: Cyclophellitol and its C3-epimer have been synthesized from5-enoglucopyranoside and 5-enomannopyranoside, respectively. The carbocyclic skeletonwas constructed through a Ferrier-II reaction meditated by PdCl2.
5 citations
TL;DR: Fluoroboronic acid adsorbed on silica gel (HBF 4 ·SiO 2 ) catalyzes the Ferrier rearrangement of per-O-acetylated glycals with alcohols and sulfonamides to give 2,3-unsaturated O- and N-glycosides in good to excellent yield and with high α-stereoselectivity as discussed by the authors.
Abstract: Fluoroboronic acid adsorbed on silica gel (HBF 4 ·SiO 2 ) catalyzes the Ferrier rearrangement of per-O-acetylated glycals with alcohols and sulfonamides to give 2,3-unsaturated O- and N-glycosides in good to excellent yield and with high α-stereoselectivity.
5 citations
TL;DR: During the authors' synthesis toward the unique nucleoside antibiotic A201A, it was surprised to find that a benzyl arabino-pent-4-enofuranoside underwent a Ferrier II-like rearrangement readily to provide the corresponding cyclopentanone derivative in high yield and stereoselectivity upon hydrogenolysis of the anomeric benzyl group.
4 citations
3 citations