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: In this paper, the total synthesis of (−)-actinobolin 2, an antipode of the natural product starting from d -glucose, was described, and a three-component coupling reaction of a functionalized cyclohexenone (+)-6, derived from d-glucoses by way of Ferrier's carbocyclization, with vinyl cuprate and an aldehyde (R)-5 effectively constructed the carbon framework of 2 in a highly stereoselective manner.
15 citations
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TL;DR: The Ferrier reaction of O-1,3-dienyl acetals promoted by organoaluminum complexes such as methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) is shown to proceed with a high degree of regio- and stereoselectivity to afford the corresponding alpha-alkenyl-substituted beta-alkoxy aldehydes in good yields.
15 citations
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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.
15 citations
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TL;DR: 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.
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.
15 citations
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TL;DR: In this paper, the Ferrier reaction of O -1,3-dienyl acetals with n-butyllithium was shown to yield α-quaternary-β,γ-unsaturated aldehydes with high α-regioselectivities.
15 citations