169310-89-8Relevant academic research and scientific papers
Highly enantioselective and regioselective catalytic dihydroxylation of homoallylic alcohol derivatives
Corey,Guzman-Perez, Angel,Noe, Mark C.
, p. 3481 - 3484 (1995)
The catalytic dihydroxylation of p-methoxyphenyl ethers of various homoallylic alcohols proceeds with excellent enantioselectivity and in the case of diolefins with regioselectivity due to the favorable influence of the aryl ether moiety, as predicted from a previously proposed transition-state model.
A General Entry to Antifeedant Sesterterpenoids: Total Synthesis of (+)-Norleucosceptroid A, (-)-Norleucosceptroid B, and (-)-Leucosceptroid K
Hugelshofer, Cedric L.,Magauer, Thomas
, p. 11351 - 11355 (2014)
The first asymmetric total synthesis of the antifeedant terpenoids (+)-norleucosceptroid A, (-)-norleucosceptroid B, and (-)-leucosceptroid K has been accomplished. This highly concise synthetic route was guided by our efforts to develop a platform for the collective synthesis of a whole family of antifeedant natural products. The synthesis features a Hauser-Kraus-type annulation followed by an unprecedented, highly efficient intramolecular dilactol aldol-type condensation reaction to produce the 5,6,5 skeleton. The developed synthetic route proceeds for norleucosceptroid A and B in 16 steps (longest linear sequence) from known compounds.
First total synthesis of (R,R,R)- and (3R,5S,9R)-bejarol by gold-catalyzed allene cycloisomerization and determination of absolute configuration of the natural product
Sawama, Yoshinari,Sawama, Yuka,Krause, Norbert
, p. 3573 - 3579 (2008)
The first total synthesis of (R,R,R)-bejarol and its (3R,5S,9R)-isomer has been accomplished which confirms the absolute configuration of the natural products. The key step is the gold-catalyzed cycloisomerization of the enantiomerically pure β-hydroxyall
PROTEIN TYROSINE PHOSPHATASE INHIBITORS AND METHODS OF USE THEREOF
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Page/Page column 360-361; 365, (2021/06/26)
Provided herein are compounds, compositions, and methods useful for inhibiting protein tyrosine phosphatase, e.g, protein tyrosine phosphatase non-receptor type 2 (PTPN2) and/or protein tyrosine phosphatase non-receptor type 1 (PTPN1), and for treating related diseases, disorders and conditions favorably responsive to PTPN1 or PTPN2 inhibitor treatment, e.g, a cancer or a metabolic disease.
7-Substituted 2-Nitro-5,6-dihydroimidazo[2,1-b][1,3]oxazines: Novel Antitubercular Agents Lead to a New Preclinical Candidate for Visceral Leishmaniasis
Thompson, Andrew M.,O’Connor, Patrick D.,Marshall, Andrew J.,Yardley, Vanessa,Maes, Louis,Gupta, Suman,Launay, Delphine,Braillard, Stephanie,Chatelain, Eric,Franzblau, Scott G.,Wan, Baojie,Wang, Yuehong,Ma, Zhenkun,Cooper, Christopher B.,Denny, William A.
supporting information, p. 4212 - 4233 (2017/06/05)
Within a backup program for the clinical investigational agent pretomanid (PA-824), scaffold hopping from delamanid inspired the discovery of a novel class of potent antitubercular agents that unexpectedly possessed notable utility against the kinetoplast
Synthesis of phosphoantigens: Scalable accesses to enantiomers of BrHPP and studies on N-HDMAPP synthesis
Bregeon, Delphine,Guillen, Frederic,Zgonnik, Viacheslav,Rivaud, Marion,Mazires, Marie-Rose,Plaquevent, Jean-Christophe,Belmant, Christian,Ferron, Laurent,Chretien, Antony,Coquerel, Gerard
supporting information, p. 5807 - 5810,4 (2020/07/30)
Phosphoantigens enable the access to a new anti-tumoral and anti-infectious therapeutic pathway, based on innate immunity through the selective activation of Tγ9δ2 lymphocytes. The first proof of concept of this new immunotherapy approach was demonstrated
Synthesis of chiral nonracemic tertiary α-thio and α-sulfonyl acetic esters via SN2 reactions of tertiary mesylates
Weaver, Jimmie D.,Morris, David K.,Tunge, Jon A.
scheme or table, p. 470 - 474 (2010/04/29)
Syntheses of enantioenriched sulfides and sulfones via substitution of tertiary mesylate with thiolate nucleophile were achieved with modest to excellent success. Georg Thieme Verlag Stuttgart New York.
Total synthesis of amphidinolide y by formation of trisubstituted (E)-double bond via ring-closing metathesis of densely functionalized alkenes
Jin, Jian,Chen, Yile,Li, Yannian,Wu, Jinlong,Dai, Wei-Min
, p. 2585 - 2588 (2008/02/08)
Amphidinolide Y, a 17-membered cytotoxic macrolide isolated from marine dinoflagellates, has been synthesized via ring-closing metathesis to assemble the congested trisubstituted (E)-double bond. The seco precursor was prepared from readily available chir
3-METHYLATED VITAMIN D DERIVATIVES
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Page 12, (2008/06/13)
An object of the present invention is to synthesize a novel vitamin D derivative having a methyl group at the 3-position.The present invention provides vitamin D derivatives represented by the general formula (1):wherein X represents -CH2-, -O- or -S-; an
The application of a mechanistic model leads to the extension of the sharpless asymmetric dihydroxylation to allylic 4-methoxybenzoates and conformationally related amine and homoallylic alcohol derivatives
Corey,Guzman-Perez, Angel,Noe, Mark C.
, p. 10805 - 10816 (2007/10/03)
The scope and utility of the Sharpless asymmetric dihydroxylation has been expanded to include the use of allylic 4-methoxybenzoates as precursors of a wide variety of substituted chiral glycerol derivatives. The allylic 4-methoxybenzoyl group was found to be superior to other allylic alcohol protecting groups with respect to both yield and enantiomeric purity of the product. For example, asymmetric dihydroxylation of allyl 4-methoxybenzoate (6a) using the (DHQD)2PYDZ·OsO4 (1·OsO4) catalyst system affords (S)-3-(4-methoxybenzoyloxy)-1,2-propanediol (7a) in >99% yield and 98% ee. The 4-methoxybenzoates of a variety of other allylic alcohols also serve as excellent substrates, in contrast to the parent alcohols themselves. The efficient asymmetric dihydroxylation of homoallylic 4-methoxyphenyl ethers (12a and 15), allyl 9-fluorenimine (18b), bis(homoallyl) 4-methoxybenzoate (14) and other structurally related substrates is also described. This methodology was developed under mechanistic guidance from the transition state model advanced earlier by us for the bis-cinchona alkaloid catalyzed asymmetric dihydroxylation reaction. The 4-methoxybenzoyl group functions not only to selectively protect one of the hydroxy groups of the product triol for subsequent synthetic manipulation but also to provide an extended binding group that participates in hydrophobic and aryl-aryl interactions with the U-shaped binding pocket of the (DHQD)2PYDZ·OsO4 catalyst (1·OsO4), thereby enhancing enantioselectivity.
