41049-30-3Relevant academic research and scientific papers
SYNTHESIS AND STRUCTURAL STUDIES OF BRIDGEHEAD DIENES 3-OXOBICYCLODODECA-1(11),8(9)-DIENE-(ZZ)-11-CARBOXYLIC ACID AND 3-OXOBICYCLOTRIDECA-1(12),9(10)-DIENE-(ZZ)-12-CARBOXYLIC ACID
Shea, K. J.,Burke, L. D.,Doedens, Robert J.
, p. 1841 - 1844 (1986)
Single crystal X-ray structures of two bridgehead dienes are reported.The bridgehead double bonds of diene 7 show only modest deviation from strain-free tetrasubstituted double bonds.The double bonds in bridgehead diene 6, however, exhibit an average deviation of the C-C=C-C torsion angle (Φ+Χ) of 14 deg.
Total synthesis of the Galbulimima Alkaloid (-)-GB17
Larson, Reed T.,Clift, Michael D.,Thomson, Regan J.
, p. 2481 - 2484 (2012)
A tale of two Michaels: The first enantioselective total synthesis of (-)-GB17 is reported. Construction of this unique naphthoquinolizinone skeleton was achieved by two stereoselective intramolecular Michael additions, one under catalyst control and the other under substrate control. Copyright
Total Synthesis of Phenanthropiperidine Alkaloids by Sequential Alkylation of N,N-Dibenzylaminoacetonitrile
Bouvry, Christelle,Cupif, Jean-Fran?ois,Franzetti, Milène,Hurvois, Jean-Pierre
, p. 6037 - 6051 (2021/12/10)
Two representative members of the phenanthropiperidine alkaloid family, tylophorine (1) and cryptopleurine (2), were synthesized by a bidirectional alkylation strategy employing dibenzylaminoacetonitrile as a substrate. This approach relies on the unprecedented condensation of metallated α-aminonitriles with bromomethylphenanthrenes to provide fully substituted α-aminonitriles, which are subjected to a NaBH4-mediated reductive decyanation process to form homobenzylic amines. From these intermediates, a terminal leaving group was introduced by simple chemical manipulation, and its displacement by a free primary amine under two favorable cyclization processes led to the formation of the future E-ring of both alkaloids in high yields. Finally, a late Pictet-Spengler cyclization ensured the formation of a D-ring for the alkaloids 1 and 2.
Selexipag intermediates and method for preparing selexipag
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, (2017/08/27)
The invention belongs to the field of chemical preparation, and relates to selexipag intermediates and a method for preparing selexipag. The selexipag intermediates are a compound SLP-4, a compound SLP-7, a compound SLP-8 and a compound SLP-10. The selexipag intermediates and the method have the advantages that the method for preparing the selexipag includes reasonable routes and is low in cost and operative difficulty and little in environmental pollution, raw materials are easily available, accordingly, requirements of large-scale industrial production can be met by the method, and the like.
Spiroacetal biosynthesis in fruit flies is complex: Distinguishable origins of the same major spiroacetal released by different Bactrocera spp.
Schwartz, Brett D.,Booth, Yvonne K.,Fletcher, Mary T.,Kitching, William,De Voss, James J.
supporting information; experimental part, p. 1526 - 1528 (2010/06/12)
The major spiroacetal ((E,E)-1) of the pestiferous fruit flies, Bactrocera tryoni and Bactrocera cucumis, is biosynthesised from fatty acids by distinguishable pathways which utilise modified β-oxidation and C-H hydroxylation, generating a putative ketodiol which cyclises. The Royal Society of Chemistry 2010.
Syntheses, characterizations, and biological activities of tetradeca-4,8-dien-1-yl acetates as sex attractants of leaf-mining moth of the genus Phyllonorycter (Lepidoptera: Gracillariidae)
Liblikas, Ilme,Mozuraitis, Raimondas,Santangelo, Ellen M.,Noreika, Remigijus,Borg-Karlson, Anna-Karin
experimental part, p. 1388 - 1403 (2010/04/23)
The four possible isomers of tetradeca-4,8-dien-1-yl acetate and corresponding alcohols were synthesized stereoselectively by synthetic routes employing Wittig coupling reaction for the preparation of (Z,E)- and (Z,Z)-isomers, and alkylation of terminal alkynes for the preparation of (E,E)- and (E,Z)-isomers as the key steps. Synthetic products were characterized by 13C- and 1H-NMR spectroscopy as well as mass-spectrometric methods. All four isomers gave distinctive mass spectra where m/z 81 fragments clearly dominated. Elution order, followed by retention index presented in parenthesis, of tetradeca-4,8-dien-1-ols was determined as (Z,Z) (2082.1), (Z,E) (2082.8), (E,E) (2083.1), and (E,Z) (2083.2) from unpolar SPB-1 column, and as (E,E) (2210.2), (Z,E) (2222.1), (E,Z) (2223.4), and (Z,Z) (2224.7) from polar DB-WAX column. The isomers of tetradeca-4,8-dien-1-yl acetates eluted in the order of (Z,Z) (2176.1), (Z,E) (2178.4), (E,Z) (2185.9), and (E,E) (2186.4) from SPB-1, and (Z,E) (2124.3), (E,E) (2157.7), (Z,Z) (2128.9), and (E,Z) (2135.9) from DB-WAX columns. Field-screening tests for attractiveness of tetradeca-4,8-dien-1-yl acetates revealed that (4Z,8E)-tetradeca-4,8-dien-1-yl acetate significantly attracted Phyllonorycter coryli and Chrysoesthia drurella males. (4E,8E)-Tetradeca-4,8-dien-1-yl acetate was the most efficient attractant for Ph. esperella and Ph. saportella males, and (4E,8Z)-tetradeca-4,8-dien-1-yl acetate was attractive to Ph. cerasicolella males.
Evaluation of aroma-active compounds in Pontianak orange peel oil (Citrus nobilis Lour. var. microcarpa Hassk.) by gas chromatography-olfactometry, aroma reconstitution, and omission test
Dharmawan, Jorry,Kasapis, Stefan,Sriramula, Praveena,Lear, Martin J.,Curran, Philip
scheme or table, p. 239 - 244 (2009/05/31)
The aroma-active compounds of Pontianak orange peel oil (Citrus nobilis Lour. var. microcarpa Hassk.) were characterized by using gas chromatography-olfactometry (GC-O) and aroma extract dilution analysis (AEDA) techniques. Forty-one compounds were found to be aroma-active, which were mainly dominated by saturated and unsaturated aldehydes. The flavor dilution (FD) factor was within the range of 2-2048, and compounds having the highest FD factor were α-pinene, β-pinene, linalool, and 2-methoxy-3-(2- methylpropyl) pyrazine, including a few unknown compounds. On the basis of GC-O results, odor activity value (OAV) and relative flavor activity (RFA) were determined for aroma model reconstitution. These resembled the original aroma of the peel oil for the green, fatty, fresh, peely, floral, and tarry attributes, with the model solution derived from OAV being the closest to Pontianak oil. Omission tests were carried out to verify the significance of (Z)-5-dodecenal and 1-phenylethyl mercaptan as key compounds in the aroma of Pontianak orange peel oil.
Retiferol derivatives and their use in the treatment of skin diseases or conditions associated with photodamage
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, (2008/06/13)
Disclosed are retiferol derivatives of formula (I): wherein X is >C═CH2 or —CH2—; Y and Z are independently of each other hydrogen, fluorine or hydroxy; A is —O(CH2)3—, —(CH2)2-(1,2-C6
Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixture synthesis
Curran, Dennis P.,Furukawa, Takashi
, p. 2233 - 2235 (2007/10/03)
(matrix presented) Four analogues made in one synthesis Four truncated analogues of the natural product discodermolide were synthesized in a single synthetic sequence. Precursors bearing four different groups at C22, each with a unique fluorous p-methoxyb
Design and synthesis of macro-heterocycles structurally related to tirofiban
Ramaseshan, Mahesh,Robitaille, Martin,Ellingboe, John W.,Dory, Yves L.,Deslongchamps, Pierre
, p. 4737 - 4742 (2007/10/03)
Sequences of nine and four steps were designed to yield two tirobifan related macrocycles by SN2 macrocyclization. The cyclic compounds contain the amino acid tyrosine, one insaturation and are either 18- or 20-membered rings. All the reaction conditions are very mild and the overall yields indicate that the results depend a lot on the structure of the targets and on the length of the reaction sequence. (C) 2000 Published by Elsevier Science Ltd.
