2612-27-3Relevant academic research and scientific papers
Synthesis of the southern furan segment of furanocembranoids
Raji Reddy, Chada,Mohammed, Siddique Z.,Gaddam, Krishna,Prapurna, Y. Lakshmi
, p. 1153 - 1158 (2019)
A convergent synthesis of the southern furan segment of novel furanocembranoids from Croton oblongifolius has been accomplished involving silver-catalyzed cyclization of alkynyl diol as the key step towards 2, 5-disubstituted furan ring formation.
Piperazine compound and application thereof in preparation of chemokine receptor CCR2 antagonist
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Paragraph 0197-0201, (2020/07/28)
The invention relates to a piperazine compound as shown in a formula (I) and an application of the piperazine compound in preparation of a chemokine receptor CCR2 antagonist or a medicine for treatingCCR2-mediated diseases.
NMDA RECEPTOR MODULATORS AND USES THEREOF
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Paragraph 00296, (2018/07/29)
Disclosed herein, in part, are heteroaromatic compounds and methods of use in treating neuropsychiatric disorders, e.g., schizophrenia and major depressive disorder. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided. The compounds are contemplated to modulate the NMDA receptor.
Optically active N- and C-terminal building blocks for the synthesis of peptidyl olefin peptidomimetics
Mirilashvili, Sima,Chasid-Rubinstein, Naama,Albeck, Amnon
experimental part, p. 4671 - 4686 (2010/10/19)
Peptidyl olefin peptidomimetics serve as biologically active compounds or as intermediates for other peptidyl isosteres. The N-terminal side of the C=C bond could be easily prepared in an optically pure form from α-amino acids. Synthesis of C-terminal building blocks in an optically pure form is more challenging. We developed a chemoenzymatic stereoselective approach to such optically active C-terminal building blocks to be assembled into peptidyl olefins by a variety of reactions. They include an electrophilic aldehyde and nucleophilic sulfone, phosphonium salt, phosphonate, and diselenide. Key enzymatic hydrolysis of prochiral diesters to the corresponding hydroxy esters introduces optical activity. The sequence of the subsequent chemical reactions, either protection- hydrolysis-functionalization or functionalization-hydrolysis- protection, determines the absolute stereochemistry of the final building blocks.
Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by α,α-diphenylprolinol trimethylsilyl ether
Boeckman Jr., Robert K.,Miller, John R.
scheme or table, p. 4544 - 4547 (2009/12/26)
The direct enantioselective hydroxymethylation of aldehydes utilizing α,α-diphenylprolinol trimethylsilyl ether as an organocatalyst is described. The intermediate α-substituted β-hydroxyaldehydes were not isolated but converted to the more readily isolab
Optically active γ-hydroxy sulfone Julia reagents for the synthesis of peptidyl olefin peptidomimetics
Mirilashvili, Sima,Chasid-Rubinstein, Naama,Albeck, Amnon
supporting information; experimental part, p. 3461 - 3464 (2009/04/14)
Peptidyl olefin peptidomimetics serve as biologically active compounds or as intermediates for other peptidyl isosteres. We developed a chemoenzymatic stereoselective approach to optically active γ-hydroxy sulfones to be assembled into peptidyl olefins by the Julia reaction. Key enzymatic hydrolysis of prochiral diesters to the corresponding hydroxy esters introduces optical activity. The sequence of the subsequent chemical reactions, either protection-hydrolysis-functionalization or functionalization-hydrolysis- protection, determines the absolute stereochemistry of the final sulfone building block. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones
Poldy, Jacqueline,Peakall, Rod,Barrow, Russell A.
, p. 2446 - 2449 (2008/09/20)
Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species.
Direct organocatalytic asymmetric α-hydroxymethylation of ketones and aldehydes
Casas, Jesús,Sundén, Henrik,Córdova, Armando
, p. 6117 - 6119 (2007/10/03)
Direct organocatalytic asymmetric α-hydroxymethylation of ketones and aldehydes with formaldehyde has been developed, which furnished the corresponding α-hydroxymethylated adducts with high chemo- and enantioselectivity. The reaction is catalyzed by proline derivatives and is a simple method for the enantioselective synthesis of α-hydroxymethylated ketones and aldehydes, and C-2 symmetric diols.
Asymmetric Schmidt reaction of hydroxyalkyl azides with ketones
Sahasrabudhe, Kiran,Gracias, Vijaya,Furness, Kelly,Smith, Brenton T.,Katz, Christopher E.,Reddy, D. Srinivasa,Aube, Jeffrey
, p. 7914 - 7922 (2007/10/03)
An asymmetric equivalent of the Schmidt reaction permits stereocontrol in ring expansions of symmetrical cyclohexanones. The procedure involves the reaction of chiral 1,2- and 1,3-hydroxyalkyl azides with ketones under acid catalysis; the initial reaction affords an iminium ether that can be subsequently opened with base. A systematic study of this reaction is reported, in which ketone substrates, chiral hydroxyalkyl azides, and reaction conditions are varied. Selectivities as high as ca. 98:2 are possible for the synthesis of substituted caprolactams, with up to 1,7-stereoselection involved in the overall process. The fact that either possible migrating carbon is electronically identical provides an unusual opportunity to study a ring-expansion reaction controlled entirely by stereoelectronic factors. The mechanism of the reaction and the source of its stereoselectivity are also discussed.
Total Synthesis of (±)-Isocembrene: A Tactic for both Diene Construction and Macrocycle Formation
Zhang, Fengzhi,Peng, Lizeng,Zhang, Tao,Mei, Tiansheng,Liu, Huawei,Li, Yulin
, p. 3761 - 3770 (2007/10/03)
The total synthesis of (±)-isocembrene 1, a naturally occurring cembrene diterpenoid, has been achieved via a unified, convergent and highly efficient strategy by imploying an intramolecular Stille sp2-sp 2 macrocyclization as the key step and it presents an ideal opportunity to extend the effectiveness of the tactic for both 1,3-diene construction and macrocycle formation.
