1720-37-2Relevant articles and documents
(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].
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.
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.
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.
