[go: up one dir, main page]

Bennani et al., 1995 - Google Patents

Syntheses of High Specific Activity 2, 3-and 3, 4-[3H] 2-9-cis-Retinoic Acid

Bennani et al., 1995

View PDF
Document ID
138917147818875838
Author
Bennani Y
Boehm M
Publication year
Publication venue
The Journal of Organic Chemistry

External Links

Snippet

The critical ring-labeling step relies on a highly regioselective tritiation of either a terminal or an isolated double bond in the presence of the conjugated retinoate side chain. Moreover, the labeling is performed at the penultimate synthetic step resulting in optimization of …
Continue reading at www.academia.edu (PDF) (other versions)

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2101/00—Systems containing only non-condensed rings
    • C07C2101/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2101/16—The ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O-metal, -CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O-metal, -CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2101/00—Systems containing only non-condensed rings
    • C07C2101/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2102/00—Systems containing two condensed rings
    • C07C2102/02—The rings having only two atoms in common
    • C07C2102/14—All rings being cycloaliphatic
    • C07C2102/22—The ring system contains eight carbon atoms (e.g. pentalene)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/23—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms

Similar Documents

Publication Publication Date Title
Bennani et al. Syntheses of High Specific Activity 2, 3-and 3, 4-[3H] 2-9-cis-Retinoic Acid
JP4001618B2 (en) Methods for modifying processes mediated by retinoid receptors and compounds useful therefor
Nicolaou et al. Stereocontrolled total synthesis of lipoxins A
Boehm et al. Synthesis of high specific activity tritium-labeled [3H]-9-cis-retinoic acid and its application for identifying retinoids with unusual binding properties
Rodrı́guez et al. First total synthesis of 7 (S), 16 (R), 17 (S)-Resolvin D2, a potent anti-inflammatory lipid mediator
Millar et al. Synthesis of Z, Z-skipped diene macrolide pheromones for Cryptolestes and Oryzaephilus grain beetles (Coleoptera Cucujidae)
Guy et al. Facile synthesis of cyclopentenone B1-and L1-type phytoprostanes
Solladie et al. Synthesis of new aromatic retinoid analogs by low-valent titanium-induced reductive elimination
Rodrı́guez et al. Total synthesis of aspirin-triggered 15-epi-lipoxin A4
US5968989A (en) Means for the modulation of processes mediated by retinoid receptors and compounds useful therefor
Rosenberger et al. Canthaxanthin. A new total synthesis
Honma et al. Development of catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfones and applications to natural product synthesis
US6992108B1 (en) Means for the modulation of processes mediated by retinoid receptors and compounds useful therefor
Sun et al. Asymmetric total synthesis of Lancifodilactone G Acetate. 1. diastereoselective synthesis of CDEFGH ring system
Vaezi et al. A conformationally defined 6-s-trans-retinoic acid isomer: synthesis, chemopreventive activity, and toxicity
Babudri et al. Novel synthetic approach to (S)-coriolic acid
Serra et al. Chemoenzymatic preparation of the p-menth-1, 5-dien-9-ol stereoisomers and their use in the enantiospecific synthesis of natural p-menthane monoterpenes
Kuwahara et al. Synthesis and absolute configuration of a cytotoxic fatty acid isolated from the mushroom, Hericium erinaceum
US5514821A (en) Ring-labeled retinoids and intermediates, and methods for their synthesis and use
Wawrzeńczyk et al. Insect growth regulators. XVI Syntheses of juvenoids with the 3, 3-dimethylcyclohexane system
Fernandes et al. Asymmetric dihydroxylation and one-pot epoxidation routes to (+)-and (−)-posticlure: a novel trans-epoxide as a sex pheromone component of Orgyia postica (Walker)
Kanamori et al. Construction of a series of intermediates in the β-oxidation pathway from THA to EPA via DHA in free acid form
Ohira Total synthesis of racemic and optically active coronafacic acids.
Schroder et al. Biradical reversion in the intramolecular photochemistry of carbonyl-substituted 1, 5-hexadienes
Srikrishna et al. Chiral synthons from α-pinene: enantioselective syntheses of bicyclo [3.3. 0] and [3.2. 1] octanones