Straightforward enantioselective synthesis of (+)-ancistrofuran

Palombo, Elie; Audran, Gérard; Monti, H.

doi:10.1016/j.tet.2005.07.087

Cited by 14 publications

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References 18 publications

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“…43 A biomimetic synthesis of acidsensitive (−)-caparrapi oxide, (+)-8-epicaparrapi oxide and (+)dysifragin has been achieved. 44,45 Enantioselective syntheses of (+)ancistrofuran 46 and (+)-ricciocarpin A 47 have been described. The generation of (E)-1-(2,3,6-trimethylphenyl)buta-1,3-diene from C 13 -norisoprenoid precursors, under wine conservation conditions, has been studied.…”

Section: Farnesanementioning

confidence: 99%

Natural sesquiterpenoids

Fraga

2006

Nat. Prod. Rep.

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Section: Farnesanementioning

confidence: 99%

Natural sesquiterpenoids

Fraga

2006

Nat. Prod. Rep.

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“…α-Keto amide 11 was the oxidative products of 10 . 14 was achieved in a two-step process via the reduction of the corresponding thionocarbonate ester derivative of 9 . Ester 12 was the methyl ester derivative of 9 .…”

Section: Resultsmentioning

confidence: 99%

Cyanohydrin as an Anchoring Group for Potent and Selective Inhibitors of Enterovirus 71 3C Protease

et al. 2015

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Cyanohydrin derivatives as enterovirus 71 (EV71) 3C protease (3C(pro)) inhibitors have been synthesized and assayed for their biochemical and antiviral activities. Compared with the reported inhibitors, cyanohydrins (1S,2S,2'S,5S)-16 and (1R,2S,2'S,5S)-16 exhibited significantly improved activity and attractive selectivity profiles against other proteases, which were a result of the specific interactions between the cyanohydrin moiety and the catalytic site of 3C(pro). Cyanohydrin as an anchoring group with high selectivity and excellent inhibitory activity represents a useful choice for cysteine protease inhibitors.

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Oxoammonium‐ and Nitroxide‐Catalyzed Oxidations of Alcohols

2009

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The discovery in 1959 of stable nitroxide‐based free radicals such as the prototypical 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) led to their use as electron spin resonance (ESR) spin labels in chemistry, biomedicine, and materials science. These nitroxides are prepared by the oxidation of secondary amines that contain no hydrogen atoms on the alpha‐carbons. The unique redox properties of nitroxides enable their use as oxidants in organic synthesis. The varied preparation and uses of oxoammonium salts as stoichiometric oxidants for alcohols are one subject of this review. Oxoammonium ions as oxidants for alcohols have a number of advantages, for example, the method is heavy‐metal free and some of the reactions can be performed in water or aqueous mixtures. A few side reactions are associated with these oxidations. The most serious is the fast reaction of the oxoammonium ion with free amines The several ways these oxidation reactions can be carried out are discussed in detail. They are: Oxidations using stoichimetric quantities of preformed oxoammonium salts carried out in either acidic, neutral, or basic conditions; reactions in which stoichiometric quantities of oxoammonium salts are generated in situ by disproportionation of a nitroxide in the presence of a strong acid; nitroxide‐catalyzed oxidations using a secondary oxidant; efficient nitroxide‐catalyzed oxidations of primary alcohols to carboxylic acids; and oxidations of primary alcohols or hemiacetals that can lead to lactones.

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Straightforward enantioselective synthesis of (+)-ancistrofuran

Cited by 14 publications

References 18 publications

Natural sesquiterpenoids

Natural sesquiterpenoids

Cyanohydrin as an Anchoring Group for Potent and Selective Inhibitors of Enterovirus 71 3C Protease

Oxoammonium‐ and Nitroxide‐Catalyzed Oxidations of Alcohols

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