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: The synthesis of enantiomerically pure decalinic structures, advanced intermediates for the synthesis of the hexahydronaphtalen part of mevinic acids, is described in this paper.
Abstract: The synthesis of enantiomerically pure decalinic structures, advanced intermediates for the synthesis of the hexahydronaphtalen part of mevinic acids, is described. The key steps are the intramolec...
TL;DR: In this paper, the conversion of 6-O-acetyl-5-enopyranosides into fully oxygenated cyclohexanones was found to proceed efficiently with a catalytic amount of palladium chloride under neutral conditions.
Abstract: The conversion of 6-O-acetyl-5-enopyranosides into fully oxygenated cyclohexanones was found to proceed efficiently with a catalytic amount of palladium chloride under neutral conditions. This method was proved to be superior in efficacy to the conventional Hg method.
TL;DR: The first total synthesis of natural product ribisin A has been achieved in 11 steps from commercially available methyl α- d -glucopyranoside with 21.6% overall yield as discussed by the authors.
Abstract: The first total synthesis of natural product ribisin A has been achieved in 11 steps from commercially available methyl α- d -glucopyranoside with 21.6% overall yield. The highly oxygenated benzofuran skeleton of this natural product was constructed, taking advantages of the inherent chirality of d -glucose, through the key reactions of Ferrier carbocyclization, Johnson iodination, Suzuki cross-coupling, and Wacker oxidative cyclization.
TL;DR: The Ferrier carbocyclization reaction is one of the most powerful transformations of carbohydrates and is particularly useful in the chiral pool synthesis of cyclohexane-containing natural products from carbohydrates as mentioned in this paper.
Abstract: The Ferrier carbocyclization reaction is one of the most powerful transformations of carbohydrates. This reaction provides enantiomerically pure cyclohexanone derivatives from aldohexoses, and is particularly useful in the chiral pool synthesis of cyclohexane-containing natural products from carbohydrates. We have investigated the synthesis of natural products utilizing the Ferrier carbocyclization reaction. This account provides a brief overview of the Ferrier carbocyclization and its application to natural product synthesis. The utility and versatility of the Ferrier carbocyclization reaction are showcased with the syntheses of hygromycin A, lycoricidine, actinobolin, galanthamine, and morphine starting from carbohydrates.
TL;DR: The Ferrier rearrangement is performed with glucal (I) and a variety of structurally different alcohols as mentioned in this paper, and it is performed in the Ferrier re-arrangement.
Abstract: The Ferrier rearrangement is performed with glucal (I) and a variety of structurally different alcohols.