37715-31-4Relevant articles and documents
A new concise synthesis of (+)-ipomeamarone, (-)-ngaione, and their stereoisomers
Usuki, Yoshinosuke,Deguchi, Taku,Iio, Hideo
, p. 1882 - 1884 (2014)
A new concise and enantiocontrolled total synthesis of (+)-ipomeamarone (1), a well-known phytoalexin, is described. The key step involved a tetrahydrofuran ring construction from optically active furyl alcohol 5 via the π-allyl palladium complex with a chiral phosphine ligand. This procedure was also applicable to the synthesis of (1)-ngaione (2) and its stereoisomers.
Diastereoselective and regioselective epoxidations of allylic alcohols by the in situ-generated dioxirane of 2,2,2-trifluoroacetophenone
Grocock, Estella L.,Marples, Brian A.,Toon, Richard C.
, p. 989 - 992 (2000)
The diastereoselective epoxidations of cyclohex-2-en-1-ols and the regioselective epoxidations of geraniol and their acetates using the in situ- generated dioxirane from 2,2,2-trifluoroacetophenone are reported along with comparable epoxidations with Oxone. (C) 2000 Elsevier Science Ltd.
INTERACTION OF 6,7-EPOXYGERANYL ACETATE AND OF 10,11-EPOXY-(E,E)-FARNESYL ACETATE WITH FLUOROSULFONIC ACID
Ungur, N. D.,Popa, N. P.,Vlad, P. F.
, p. 613 - 617 (1993)
The interaction of 6,7-epoxygeranyl acetate and of 10,11-epoxy-(E,E)-farnesyl acetate with fluorosulfonic acid forms isomerization products and products of the opening of the epoxide rings.
Synthese, 1H-NMR- und CD-Studien von (S)-1,2-Epoxy-1,2-dihydrolycopin und (S)-1',2'-Epoxy-1',2'-dihydro-γ-carotin
Kamber, Matthias,Pfander, Hanspeter,Noack, Klaus
, p. 968 - 985 (1984)
The synthesis of (S)-1,2-epoxy-1,2-dihydrolycopene ((S)-1) and (S)-1',2'-epoxy-1',2'-dihydro-γ-carotene ((S)-2) are described.The CD spectra of the (all-E)-isomers and of the isomers (7Z,S)-1 and (7'Z,S)-2 are discussed.The comparison of the CD spectra of the synthetic (S)-1 and the compound isolated from the tomatoes proves the (S)-configuration of the natural product.
Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid-Producing Plants
Partridge, Suzanne J.,Withall, David M.,Caulfield, John C.,Pickett, John A.,Stockman, Robert A.,Oldham, Neil J.,Birkett, Michael A.
supporting information, p. 7231 - 7234 (2021/04/21)
Biosynthesis of (1R,4aS,7S,7aR)-nepetalactol (1) and (4aS,7S,7aR)-nepetalactone (2) in plants involves iridoid synthase (ISY), an atypical reductive cyclase that catalyses the reduction of 8-oxogeranial into the reactive enol of (S)-8-oxocitronellal, and cyclization of this enol intermediate, either non-enzymatically or by a nepetalactol-related short chain dehydrogenase enzyme (NEPS) that yields the nepetalactols. In this study, we investigated the biosynthesis in vivo of 1 and 2 in the pea aphid, Acyrthosiphon pisum, using a library of isotopically-labelled monoterpenoids as molecular probes. Topical application of deuterium-labelled probes synthesized from geraniol and nerol resulted in production of 2H4?lactol 1 and 2H4?lactone 2. However, deuterium incorporation was not evident using labelled probes synthesized from (S)-citronellol. These results suggest that iridoid biosynthesis in animals, specifically aphids, may follow a broadly similar route to that characterised for plants.
Rapid Oxidation Indoles into 2-Oxindoles Mediated by PIFA in Combination with n-Bu4NCl ? H2O
Liang, Peng,Zhao, Hang,Zhou, Tingting,Zeng, Kaiyun,Jiao, Wei,Pan, Yang,Liu, Yazhou,Fang, Dongmei,Ma, Xiaofeng,Shao, Huawu
supporting information, p. 3532 - 3538 (2021/06/09)
We report the development of a rapid approach for directly converting indoles into 2-oxindoles promoted by HOCl formed in situ from the combination of (bis(trifluoroacetoxy) iodo)benzene (PIFA) and n-Bu4NCl ? H2O. The procedure is widely functional group tolerant and provides 2-oxindoles in up to 95% yield within 5 min. The potential applications of the developed methodology are demonstrated by the gram-scale preparation of 3-methyl-2-oxindole (11 a), the one-pot two-step syntheses of spiro-oxindoles 26 a and 26 b, and the formal synthesis of (-)-folicanthine (2). (Figure presented.).
Total Synthesis of (±)-Leonuketal
Brimble, Margaret A.,Furkert, Daniel P.,Grant, Phillip S.
supporting information, (2020/11/18)
Leonuketal is an 8,9-seco-labdane terpenoid with a unique tetracyclic structure, owing to a diversity-generating biosynthetic C-C bond cleavage event. The first total synthesis of leonuketal is reported, featuring a Ti(III)-mediated reductive cyclization of an epoxy nitrile ether, an unusual ring-opening alkyne formation as part of an auxiliary ring strategy, and the previously undescribed Au(I)-catalyzed cyclization of a β-keto(enol)lactone to assemble the core spiroketal motif.
Enantioselective Bio-Hydrolysis of Geranyl-Derived rac-Epoxides: A Chemoenzymatic Route to trans-Furanoid Linalool Oxide
van Lint, Matthijs J.,Gümüs, Aysegül,Ruijter, Eelco,Faber, Kurt,Orru, Romano V. A.,Hall, Mélanie
, p. 813 - 825 (2019/01/04)
In contrast to many chemical dihydroxylation methods, enzymatic epoxide hydrolysis provides an environmentally benign route to vicinal diols, which are important intermediates in the synthesis of fine chemicals and pharmaceuticals. Using epoxide hydrolases, enantiopure diols are accessible under mild conditions. In order to assess the selectivity of epoxide hydrolases on geraniol-derived oxiranes, a range of derivatives were screened against a large variety of enzyme preparations. For nearly all substrates, a matching hydrolase with excellent enantioselectivity (≥95% ee) could be found. In addition, a chemoenzymatic approach for the stereoselective synthesis of furanoid linalool oxide was developed. Combination of enzymatic enantioselective hydrolysis with stereoselective Tsuji-Trost reaction granted diastereoselective access to trans-(2R,5R)-configured linalool oxide with high diastereomeric and enantiomeric excess (97% de and 97% ee). (Figure presented.).
Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants
Nasrallah, Ali,Grelier, Gwendal,Lapuh, Maria Ivana,Duran, Fernando J.,Darses, Benjamin,Dauban, Philippe
supporting information, p. 5836 - 5842 (2018/11/24)
Dirhodium(II) complexes and iodine(III) oxidants have found useful applications in synthetic nitrene chemistry. In this study, the combination of the dirhodium(II) complex Rh2(tpa)4 (tpa = triphenylacetate) with the iodine(III) oxidant PhI(OPiv)2 is shown to promote the epoxidation of alkenes in the presence of 2 equivalents of water. The reaction can be applied to diversely substituted alkenes and the corresponding epoxides are isolated with yields of up to 90 %. A possible mechanism involves the dirhodium(II) complex as a Lewis acid species that would tune the oxidizing character of the iodine(III) reagent.
Selective PPARδ Modulators Improve Mitochondrial Function: Potential Treatment for Duchenne Muscular Dystrophy (DMD)
Lagu, Bharat,Kluge, Arthur F.,Tozzo, Effie,Fredenburg, Ross,Bell, Eric L.,Goddeeris, Matthew M.,Dwyer, Peter,Basinski, Andrew,Senaiar, Ramesh S.,Jaleel, Mahaboobi,Tiwari, Nirbhay Kumar,Panigrahi, Sunil K.,Krishnamurthy, Narasimha Rao,Takahashi, Taisuke,Patane, Michael A.
supporting information, p. 935 - 940 (2018/09/06)
The X-ray structure of the previously reported PPARδ modulator 1 bound to the ligand binding domain (LBD) revealed that the amide moiety in 1 exists in the thermodynamically disfavored cis-amide orientation. Isosteric replacement of the cis-amide with five-membered heterocycles led to the identification of imidazole 17 (MA-0204), a potent, selective PPARδ modulator with good pharmacokinetic properties. MA-0204 was tested in vivo in mice and in vitro in patient-derived muscle myoblasts (from Duchenne Muscular Dystrophy (DMD) patients); 17 altered the expression of PPARδ target genes and improved fatty acid oxidation, which supports the therapeutic hypothesis for the study of MA-0204 in DMD patients.
