1720-37-2Relevant academic research and scientific papers
(4E,8Z)-12-methyloxacyclotetradeca-4,8-dien-2-one and its 7a-homologue: Conformationally constrained double-unsaturated macrocyclic musks by ring-closing alkyne metathesis
Kraft, Philip,Berthold, Carola
, p. 543 - 550 (2008)
The double-unsaturated macrocyclic lactones (4E,8Z)-12- methyloxacyclotetradeca-4,8-dien-2-one and its 7a-homologue (4E,9Z)-13- methyloxacyclopentadeca-4,9-dien-2-one, designed as new potent musk odorants by molecular modeling, were synthesized by ring-closing alkyne metathesis in the presence of 10 mol% of Schrock's alkylidyne catalyst, and subsequent Lindlar hydrogenation. Demethylation of citronellol, induced by nitrous acid, afforded the 3-methyloct-6-yn-1-ol building block. The substrates for the alkyne metathesis were prepared by Steglich esterification of citronellol with the 3E-configured non-3-en-7-ynoic and dec-3-en-8-ynoic acids, accessible by β,γ-selective Knoevenagel condensation from the corresponding alkynals hept-5-ynal and oct-6-ynal, which were synthesized by Eschenmoser-Ohloff fragmentation of the epoxide of 2-methylcyclohex-2-enone, and methylation of hex-5-yn-1-ol, respectively. Both target structures, (4E,8Z)-12-methyloxacyclotetradeca-4,8-dien-2-one and its 7a-homologue, emanated most pleasant and powerful musk odors. Georg Thieme Verlag Stuttgart.
An Alkyne-Metathesis-Based Approach to the Synthesis of the Anti-Malarial Macrodiolide Samroiyotmycin A
Fürstner, Alois,Grimes, Mark I.,Hulme, Alison N.,Whitelegge, James T.,Yiannakas, Ektoras
, p. 18504 - 18508 (2021)
We report the first total synthesis of samroiyotmycin A (1), a C2-symmetric 20-membered anti-malarial macrodiolide isolated from Streptomyces sp. The convergent synthetic strategy orchestrates bisalkyne fragment-assembly using an unprecedented Sch?llkopf-type condensation on a substituted β-lactone and an ambitious late-stage one-pot alkyne cross metathesis–ring-closing metathesis (ACM–RCAM) reaction. The demanding alkyne metathesis sequence is achieved using the latest generation of molybdenum alkylidynes endowed with a tripodal silanolate ligand framework. Subsequent conversion to the required E-alkenes uses contemporary hydrometallation chemistry catalysed by tetrameric cluster [{Cp*RuCl}4].
The (5Z)-5-Pentacosenoic and 5-Pentacosynoic Acids Inhibit the HIV-1 Reverse Transcriptase
Moreira, Lizabeth Giménez,Orellano, Elsie A.,Rosado, Karolyna,Guido, Rafael V. C.,Andricopulo, Adriano D.,Soto, Gabriela Ortiz,Rodríguez, José W.,Sanabria-Ríos, David J.,Carballeira, Néstor M.
, p. 1043 - 1050 (2015)
The natural fatty acids (5Z)-5-pentacosenoic and (9Z)-9-pentacosenoic acids were synthesized for the first time in eight steps starting from either 4-bromo-1-butanol or 8-bromo-1-butanol and in 20-58 % overall yields, while the novel fatty acids 5-pentacosynoic and 9-pentacosynoic acids were also synthesized in six steps and in 34-43 % overall yields. The ?5 acids displayed the best IC50's (24-38 μM) against the HIV-1 reverse transcriptase (RT) enzyme, comparable to nervonic acid (IC50 = 12 μM). The ?9 acids were not as effective towards HIV-RT with the (9Z)-9-pentacosenoic acid displaying an IC50 = 54 μM and the 9-pentacosynoic acid not inhibiting the enzyme at all. Fatty acid chain length and position of the unsaturation was important for the observed inhibition. None of the synthesized fatty acids were toxic (IC50 > 500 μM) towards peripheral blood mononuclear cells. Molecular modeling studies indicated the structural determinants underlying the biological activity of the most potent compounds. These results provide new insights into the structural requirements that must be present in fatty acids so as to enhance their inhibitory potential towards HIV-RT.
A Tandem Synthesis of (+/-)-Euphococcinine and (+/-)-Adaline
Davison, Edwin C.,Holmes, Andrew B.,Forbes, Ian T.
, p. 9047 - 9050 (1995)
Intramolecular hydroxylamine-alkyne cyclisation of the hydroxylamines 8 and 9 afforded six-membered cyclic nitrones which without isolation underwent a tandem intramolecular dipolar cycloaddition to produce the tricyclic isoxazolidines 6 and 7 respectively.These were converted in two steps into the ladybird defence alkaloids (+/-)-euphococcinine 4 and (+/-)-adaline 5.
Scope and Mechanism of Stannylalumination of 1-Alkynes
Sharma, Sunaina,Oehlschlager, Allan C.
, p. 5064 - 5073 (1989)
Terminal acetylenes react with Bu3SnAlEt2 in the presence of Cu+ or Pd0 catalysts to give 1,2-dimetallo-1-alkenes in highly regio- and stereoselective reactions.These intermediates can be selectively functionalized at the vinyl-aluminum bond to provide vinylstannanes, which upon transmetalation and further reaction with electrophiles give stereodefined trisubstituted olefins.In sharp contrast to the normal behavior of alkylaluminum reagents, this process tolerates a number of functional groups including OH, OAc, OTHP, and Br.Mechanistic investigations suggest that the addition of Bu3SnAlEt2 to 1-alkynes proceeds via stannylcupration followed by capture of the stannylcuprate adduct by electrophilic aluminum.
Additions of CuCN-Derived Stannylcuprates to Terminal Alkynes: A Comparative Spectroscopic and Chemical Study
Singer, Robert, D.,Hutzinger, Michael W.,Oehlschlager, Allan C.
, p. 4933 - 4938 (1991)
The stannylcupration of terminal alkynes 4a,b with cuprates 1-3 proceeds rapidly and reversibly above -35 deg C to afford stannylcuprate intermediates 5a,b and 6a,b.These intermediates have been characterized by 2H and 13C NMR labelling experiments.Corroborating evidence for this reversible addition comes from further chemical tests and cross-over experiments that show the thermodynamic favorability of the adducts.Further comparative study of reaction products and byproducts shows 2 to be the stannylcuprate of choice for the preparation of vinylstannates from terminal alkynes.
PYRAZOLO[1,5-D][1,2,4]TRIAZINE-5(4H)-ACETAMIDES AS INHIBITORS OF THE NLRP3 INFLAMMASOME PATHWAY
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Page/Page column 107, (2021/10/22)
The invention relates to novel compounds for use as inhibitors of NLRP3 inflammasone production, wherein such compounds are as defined by compounds of formula (I) and wherein the integers R1, R2 and R3 are defined in the description, and where the compounds may be useful as medicaments, for instance for use in the treatment of a disease or disorder that is associated with NLRP3 inflammasome activity.
FATTY ACID COMPOUND, PREPARATION METHOD THEREFOR AND USE THEREFOR
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Paragraph 0117-0119, (2019/02/19)
The present invention relates to a class of fatty acid compounds, a preparation method thereof and use thereof. The fatty acid compounds have the structure of the formula I, which has the ability to activate APMK and inhibit the glucose output in mouse primary hepatocytes. The fatty acid compounds can be used in preparing a medicament for the treatment of obesity or diabetes.
Efficient synthesis of (5Z,7E)-Dodecadienal, the sex pheromone of the european pine moth dendrolimus pini
T?t?s, ?tefania,Vasian, Iuliana,Gorgan, Monica,T?t?s, Róbert,Lar, Claudia
, p. 315 - 319 (2018/10/20)
Efficient synthesis of (5Z,7E)-dodecadienal, the sex pheromone of European pine moth Dendrolimus pini, was stereoselectively accomplished via Pd- and Fe- catalyzed cross-coupling reactions in the key steps. The very simple and practical method developed herein provides a general synthetic approach to other (Z,E)-diene compounds.
Synthetic method for attractant component namely cis,trans-5,7-dodecadiene derivative in Dendrolimus sex pheromone
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Paragraph 0015; 0027-0030, (2019/01/08)
The invention discloses a synthetic method for an attractant component namely a cis,trans-5,7-dodecadiene derivative in Dendrolimus sex pheromone. With the synthetic method provided by the invention,5-hexyne-1-ol and 3, 4-dihydro-2H-pyran used as starting materials are successively subjected to an addition reaction, a condensation reaction, an elimination reaction, a hydrogenation reaction, a deprotection reaction and a derivatization reaction to obtain the cis,trans-5,7-dodecadiene derivative. The synthetic method provided by the invention has the advantages of short route, high reaction yield in each step, simple operation and convenience in mass production.
