90719-27-0Relevant academic research and scientific papers
Silent catalytic promiscuity in the high-fidelity terpene cyclase δ-cadinene synthase
Loizzi, Marianna,Miller, David J.,Allemann, Rudolf K.
, p. 1206 - 1214 (2019/02/07)
δ-Cadinene synthase (DCS) is a high-fidelity sesquiterpene synthase that generates δ-cadinene as the sole detectable organic product from its natural substrate (E,E)-FDP. Previous work with this enzyme using substrate analogues revealed the ability of DCS
Synthesis and evaluation of locostatin-based chemical probes towards PEBP-proteins
Hoogenboom, Jorin,Fiers, Martijn,Immink, Richard,Zuilhof, Han,Wennekes, Tom
supporting information, p. 2406 - 2409 (2016/05/19)
Phosphatidyl ethanolamine-binding proteins (PEBPs) are implicated in various critical physiological processes in all eukaryotes. Among them is Flowering Locus T (FT), the protein recently discovered as the vital flowering hormone in plants. Small molecule
Conjugate hydrotrifluoromethylation of α,β-unsaturated acyl-oxazolidinones: Synthesis of chiral fluorinated amino acids
Erdbrink, Holger,Peuser, Ilona,Gerling, Ulla I. M.,Lentz, Dieter,Koksch, Beate,Czekelius, Constantin
supporting information, p. 8583 - 8586 (2013/01/15)
A novel conjugate hydrofluoroalkylation of α,β-unsaturated acyl-oxazolidinones is described. Using this method, enantiomerically pure β-trifluoromethylated amino acids were prepared. Trifluorovaline and trifluoroisoleucine were incorporated into peptides and found to show extremely low α-helix propensities.
Asymmetric synthesis of isoquinuclidines by Diels-Alder reaction of 1,2-dihydropyridine utilizing a chiral Lewis acid catalyst
Seki, Chigusa,Hirama, Masafumi,Hutabarat, N.D.M. Romauli,Takada, Junko,Suttibut, Chonticha,Takahashi, Hideto,Takaguchi, Takuya,Kohari, Yoshihito,Nakano, Hiroto,Uwai, Koji,Takano, Nobuhiro,Yasui, Mitsukuni,Okuyama, Yuko,Takeshita, Mitsuhiro,Matsuyama, Haruo
experimental part, p. 1774 - 1781 (2012/03/10)
The chiral isoquinuclidine derivative, 2-azabicyclo[2.2.2]octane ring system, endo-(7R)-3 was obtained in good yield with excellent diastereoselectivity (up to 92% de) by Diels-Alder reaction of 1-(phenoxycarbonyl)-1,2-dihydropyridine 1 with N-acryloyl-(4S)-4- benzyloxazolidin-2-one (4S)-2 using titanium-(2R,3R)-TADDOLate 4 as a chiral Lewis acid catalyst in toluene at 0 °C. On the other hand, endo-(7S)-3 was obtained in good yield with excellent diastereoselectivity (up to 97% de) by Diels-Alder reaction of 1 with (4R)-2 using Cu(OTf)2/(4S,4′S)- bis(oxazoline) catalyst 8 as a chiral Lewis acid catalyst in dichloromethane at 0 °C. In these reactions, the choice of solvent and the combination of titanium-(2R,3R)-TADDOLate 4 {or Cu(II)/(4S,4′S)-bis(oxazoline) 8} and dienophile (4S)-2 {or (4R)-2} are very important. The stereochemistry of endo-(7R)-3 has been established to be (1R,4S,7R) and the reaction mechanism is proposed.
Diastereoselective aziridination of chiral electron-deficient olefins with N-chloro-N-sodiocarbamates catalyzed by chiral quaternary ammonium salts
Murakami, Yuta,Takeda, Youhei,Minakata, Satoshi
experimental part, p. 6277 - 6285 (2011/10/02)
Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the
Enantioselective synthesis of α-methylene-β-hydroxy carboxylic acid derivatives via a diastereoselective aldol/β-elimination sequence: Application to the C(15)-C(21) fragment of tedanolide C
Barth, Roland,Roush, William R.
supporting information; experimental part, p. 2342 - 2345 (2010/07/13)
An enantioselective synthesis of α-methylene-β-hydroxy carboxylic acid derivatives via a highly diastereoselective, one-pot syn-aldol and β-elimination sequence utilizing the chiral β-(phenylselenyl) propionyl imide 15 is described. This new method, which constitutes an alternative to the Baylis-Hillman reaction, has been applied to the synthesis of the C(15)-C(21) fragment of tedanolide C.
Towards functionalized silicon-containing α-amino acids: Asymmetric syntheses of sila analogs of homoserine and homomethionine
Smith, Richard J.,Bienz, Stefan
, p. 1681 - 1696 (2007/10/03)
The homoserine and homomethionine sila analogs, (R)-HOSi(Me 2)CH2CH(NH2)CO2H ((R)-21) and (R)-MeSCH2Si(Me2)CH2CH(NH2)CO 2H ((R)-24), respectively, were each synthesized in nine steps and in 30 and 23% overall yield, respectively, from commercially available ClSiMe 2CH2Cl. The key step of both syntheses was the asymmetric α-bromination of an Evans amide to introduce the stereogenic center of the amino acids with defined absolute configuration. While the preparation of the homomethionine analog (R)-24 followed the expected pathway, the sila analog of homoserine, (R)-21, was unexpectedly formed during the catalytic hydrogenation of an N3CH2-substituted silane derivative.
2-OXAZOLIDINONES AND THEIR USE AS INHIBITORS OF ANIMAL CELL MOTILITY AND GROWTH
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Page 53; 67, (2010/11/30)
Cell motility and growth inhibitors, including compounds of the general structural formula (I), and use of the cell motility and cell growth inhibitors, and pharmaceutically acceptable salts, pro-drugs, and solvates thereof, as therapeutic agents, are disclosed.
Total synthesis of a conformationally constrained didemnin B analog
Xiao,Vera,Liang,Joullie
, p. 2734 - 2742 (2007/10/03)
The total synthesis of a didemnin B analogue containing a conformationally constrained replacement for the isostatine moiety is reported. Synthetic highlights include an improved preparation of 2-hydroxy-3-cyclohexenecarboxylic acid and a new strategy for accessing the macrocycle.
