78513-07-2Relevant articles and documents
Formal synthesis of borrelidin: A highly enantio- and diastereoselective access to the Morken's C2-C12 intermediate
Gembus, Vincent,Karmazin, Lydia,Uguen, Daniel,Zoller, Thomas
supporting information, p. 359 - 380 (2019/02/25)
In contrast to methyl and isobutyl phenyl sulfone, condensing under basic conditions higher alkyl sulfones and trans-2,3-epoxy-butanol 13c (or its O-benzyl and O-silyl derivatives) proved unfeasible, a difficulty that was overcome by using mono ethers of trans-2,3-epoxy-butane-1,4-diol 35c as the electrophilic reagents. Thus, adding excess BuLi to a mixture of the benzyl ether 35b and sulfone ent-12a, a stereodiad sulfone prepared in pure state from the R-Roche ester, via the O-trityloxy-sulfone ent-12c (X-ray), gave, after elimination by column chromatography of the side-formed regioisomer, a diolsulfone that was next converted to sulfone 20 by means of conventional functional-group modifications. Reacting like-wise this sulfone with the parent O-PMB derivative 35a, and then proceeding to the same purification process and function adjustment, delivered the title fragment in virtually pure state.
Novel autophagy modulators: Design and synthesis of (+)-epogymnolactam analogues and structure-activity relationship
Ueda, Kazuki,Okado, Yuji,Shigetomi, Kengo,Ubukata, Makoto
, p. 5159 - 5168 (2018/09/27)
(+)-Epogymnolactam (1) was discovered as a novel autophagy inducer from a culture of Gymnopus sp. in our laboratory. To determine structure-activity relationships among (+)-epogymnolactam analogues comparing with cerulenin (2), we synthesized 5 analogues
Stereoselective synthesis of orthogonally protected 2,3-disubstituted morpholines using a base-catalysed cascade reaction
Marlin, Frederic J.
supporting information, p. 3078 - 3080 (2017/07/17)
The stereoselective synthesis of differentially protected [3-(hydroxymethyl)morpholin-2-yl]methanols is described, starting from chiral epoxides. The key step involves a one-pot oxazolidinone formation via intramolecular epoxide opening and concomitant cy
HIV PROTEASE INHIBITORS
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Page/Page column 37, (2015/07/07)
The present invention is directed to 2,5,6-substituted morpholine derivatives and their use in the inhibition of HIV protease, the inhibition of HIV replication, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis,
Stereoselective total synthesis of oplopandiol, oploxyne A, and oploxyne B
Reddy, B.V. Subba,Nageshwar Rao,Kumaraswamy,Yadav
supporting information, p. 4590 - 4592 (2014/12/10)
A stereoselective total synthesis of oplopandiol, oploxyne A, and (-)-oploxyne B is described. The key reactions include Sharpless asymmetric epoxidation, d-proline catalyzed aminoxylation, Cadiot-Chodkiewicz cross-coupling reaction, m-CPBA induced substrate-controlled stereoselective epoxidation, and Lewis acid catalyzed stereo- and regioselective ring-opening of epoxide.
Palladium hydroxide catalyzed transformation of primary propargylic alcohols into aldehydes: Application to the synthesis of the tetrahydrofuran core
Sabitha, Gowravaram,Reddy, A.Yagundar,Nayak, Sambit,Yadav, Jhillu S.
scheme or table, p. 1657 - 1662 (2012/07/03)
A palladium-catalyzed one-pot, two-step sequence involving redox isomerization/reduction of primary propargylic alcohols into the corresponding aldehydes has been achieved at room temperature for the first time in good to excellent yields under mild conditions. The functional group compatibility in this reaction is studied and this new methodology has been successfully applied in the synthesis of the 2,5-trans-tetrahydrofuran ring system of amphidinolides. It is noteworthy that aromatic substituted propargylic alcohols gave a mixture of unsaturated and saturated aldehydes, whereas aliphatic propargylic alcohols gave only saturated aldehydes. Georg Thieme Verlag Stuttgart · New York.
Organocatalytic asymmetric epoxidation and tandem epoxidation/Passerini reaction under eco-friendly reaction conditions
Deobald, Anna Maria,Corrêa, Arlene G.,Rivera, Daniel G.,Paix?o, Márcio Weber
, p. 7681 - 7684 (2013/04/24)
An eco-friendly synthesis of highly functionalized epoxides and their incorporation into an organocatalytic multicomponent approach are reported. For this, a modified class of diarylprolinol silyl ethers was designed to enable high catalytic activity in an environmentally benign solvent system. The one-pot procedure showed great efficiency in promoting stereoselective multicomponent transformations in a tandem, 'green' fashion. Because of its non-residual, efficient and selective character, this synthetic design shows promise for large-scale applications in both diversity and target-oriented syntheses. The Royal Society of Chemistry 2012.
Highly diastereoselective construction of substituted pyrrolidines: Formal synthesis of (-)-bulgecinine
Das, Biswanath,Kumar, Duddukuri Nandan
scheme or table, p. 1285 - 1287 (2011/07/09)
A highly diastereoselective synthesis of substituted pyrrolidines has been achieved starting from nonchiral molecule, allyl bromide, or cis-but-2-ene-1,4-diol. The method involves the asymmetric epoxidation and endo-mode epoxide opening with azide nucleop
Stereoselective formal total synthesis of novel antibiotic (-)-centrolobine
Mohapatra, Debendra K.,Pal, Rita,Rahaman, Hasibur,Gurjar, Mukund K.
body text, p. 219 - 227 (2010/05/03)
A concise and stereoselective formal total synthesis of (-)-centrolobine is achieved utilizing Mioskowski's Lewis acid mediated epoxide opening followed by ring-closing metathesis as the key reaction.
Stereocontrolled construction of tetrasubstituted tetrahydrofurans: Synthesis of 2,5-anhydro d-glucitol
Das, Biswanath,Kumar, Duddukuri Nandan
scheme or table, p. 6011 - 6013 (2010/11/21)
A highly stereoselective construction of 2,3,4,5-tetrasubstituted tetrahydrofurans has been accomplished by an unusual intramolecular 5-endo-tet cyclization of 2,3-epoxy alcohols involving hydroxyl nucleophile. The method has been utilized for the synthes
