86884-89-1Relevant academic research and scientific papers
SYNTHESIS OF NATURAL AND UNNATURAL FRONTALIN
Hosokawa, Takahiro,Makabe, Yoshiki,Shinohara, Toru,Murahashi, Shun-Ichi
, p. 1529 - 1530 (1985)
(S)-(-)- and (R)-(+)-Frontalin were synthesized, respectively, in high enantiomer excess from β-methallyl alcohol (2) by three-step procedure; (i) asymmetric epoxidation of 2, (ii) the epoxide opening with homoallylmagnesium bromide, and (iii) Pd(II)-catalyzed intramolecular acetalization.
Development of a scalable process for the synthesis of DNDI-VL-2098: A potential preclinical drug candidate for the treatment of visceral leishmaniasis
Satam, Vijay S.,Pedada, Srinivasa Rao,Kamaraj, Pasumpon,Antao, Nakita,Singh, Apoorva,Hindupur, Rama Mohan,Pati, Hari N.,Thompson, Andrew M.,Launay, Delphine,Martin, Denis
, p. 52 - 59 (2017)
A process suitable for kilogram-scale synthesis of (2R)-2-methyl-6-nitro-2-{[4-(trifluoromethoxy)phenoxy]- methyl}-2,3-dihydroimidazo[2,1-b][1,3]oxazole (DNDI-VL-2098, 2), a preclinical drug candidate for the treatment of visceral leishmaniasis, is described. The four-step synthesis of the target compound involves the Sharpless asymmetric epoxidation of 2- methyl-2-propen-1-ol, 8. Identification of a suitable synthetic route using retrosynthetic analysis and development of a scalable process to access several kilograms of 2 are illustrated. The process was simplified by employing in situ synthesis of some intermediates, reducing safety hazards, and eliminating the need for column chromatography. The improved reactions were carried out on the kilogram scale to produce 2 in good yield, high optical purity, and high quality.
Nitroimidazole compound as well as preparation method and application thereof
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Paragraph 0112-0115; 0116-0117, (2021/02/10)
The invention discloses a novel nitroimidazole compound as well as a preparation method and application thereof. The nitroimidazole compound has a general formula (I) shown in the specification.
CARBAZOLE-CONTAINING AMIDES, CARBAMATES, AND UREAS AS CRYPTOCHROME MODULATORS
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Paragraph 0350, (2015/10/28)
The subject matter herein is directed to carbazole-containing amide, carbamate, and urea derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R1, R2, R3, R4, R5, R6, R7, A, D, E, G, J, L, M, Q, a, and b are accordingly described. Also provided are pharmaceutical compositions containing the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, complications associated with diabetes, Cushing's syndrome, NASH, NAFLD, asthma, and COPD.
Novel pathway for the synthesis of arylpropionamide-derived selective androgen receptor modulator (SARM) metabolites of andarine and ostarine
Schragl, Katharina M.,Forsdahl, Guro,Gmeiner, Guenter,Enev, Valentin S.,Gaertner, Peter
supporting information, p. 2239 - 2242 (2013/05/09)
O-Dephenylandarine and O-dephenylostarine, two SARM metabolites relevant for doping control analysis, were synthesized in their endogenous (S)-forms as well as in terms of their racemates. The enantiopure (S)-metabolites were obtained after six steps in 20% and 23% overall yield, the slightly modified racemic route provided the compounds in 28% and 31% total yield, respectively.
Asymmetric synthesis of α-Tocopherol
Hengartner, Urs,Chougnet, Antoinette,Liu, Kegang,Woggon, Wolf-D.
experimental part, p. 1306 - 1311 (2010/06/12)
α-Tocopherol was synthesized from a chiral intermediate α-hydroxy ester by means of two ring-closing methods to yield the chromanol in 94 % diastereomeric excess.
Development of a multikilogram synthesis of a chiral epoxide precursor to a CCR1 antagonist. Use of in situ monitoring for informed optimisation via fragile intermediates
Ange, Debra,Booker, James E. M.,Pedge, Nicholas,Sinclair, Rhona,Sleigh, Chris,Stefinovic, Marijan,Vaz, Luis-Manuel,Way, Edward
scheme or table, p. 72 - 84 (2010/05/02)
The optimisation and scale up of a manufacturing route to a key intermediate, acetic acid 4-acetylamino-3-(2-methyl-oxiranyl- methoxy)phenyl ester (2), utilising a SNAr coupling, the hydro- genation of a nitro moiety and the conversion of a chi
Asymmetric synthesis of (+)-polyanthellin A
Campbell, Matthew J.,Johnson, Jeffrey S.
body text, p. 10370 - 10371 (2009/12/23)
(Chemical Equation Presented) A concise and convergent route to (+)-polyanthellin A is presented. This synthesis features a diastereoselective cyclopropane/aldehyde [3+2] cycloaddition to install the hydroisobenzofuran core. The use of MADNTf2
Spongipyran synthetic studies. Evolution of a scalable total synthesis of (+)-spongistatin 1
Smith III, Amos B.,Sfouggatakis, Chris,Risatti, Christina A.,Sperry, Jeffrey B.,Zhu, Wenyu,Doughty, Victoria A.,Tomioka, Takashi,Gotchev, Dimitar B.,Bennett, Clay S.,Sakamoto, Satoshi,Atasoylu, Onur,Shirakami, Shohei,Bauer, David,Takeuchi, Makoto,Koyanagi, Jyunichi,Sakamoto, Yasuharu
supporting information; scheme or table, p. 6489 - 6509 (2011/02/25)
Three syntheses of the architecturally complex, cytotoxic marine macrolide (+)-spongistatin 1 (1) are reported. Highlights of the first-generation synthesis include: use of a dithiane multicomponent linchpin coupling tactic for construction of the AB and CD spiroketals, and their union via a highly selective Evans boron-mediated aldol reaction en route to an ABCD aldehyde; introduction of the C(44)-C(51) side chain via a Lewis acid-mediated ring opening of a glucal epoxide with an allylstannane to assemble the EF subunit; and final fragment union via Wittig coupling of the ABCD and EF subunits to form the C(28)-C(29) olefin, followed by regioselective Yamaguchi macrolactonization and global deprotection. The second- and third-generation syntheses, designed with the goal of accessing 1 g of (+)-spongistatin 1 (1), maintain both the first-generation strategy for the ABCD aldehyde and final fragment union, while incorporating two more efficient approaches for construction of the EF Wittig salt. The latter combine the original chelation-controlled dithiane union of the E- and F-ring progenitors with application of a highly efficient cyanohydrin alkylation to append the F-ring side chain, in conjunction with two independent tactics to access the F-ring pyran. The first F-ring synthesis showcases a Petasis-Ferrier union/rearrangement protocol to access tetrahydropyrans, permitting the preparation of 750 mg of the EF Wittig salt, which in turn was converted to 80 mg of (+)-spongistatin 1, while the second F-ring strategy, incorporates an organocatalytic aldol reaction as the key construct, permitting completion of 1.009 g of totally synthetic (+)-spongistatin 1 (1). A brief analysis of the three syntheses alongside our earlier synthesis of (+)-spongistatin 2 is also presented.
Development and application of versatile bis-hydroxamic acids for catalytic asymmetric oxidation
Barlan, Allan U.,Zhang, Wei,Yamamoto, Hisashi
, p. 6075 - 6087 (2008/02/03)
In this article, we describe the development and preliminary results of our new designed C2-symmetric bis-hydroxamic acid (BHA) ligands and the application of the new ligands for vanadium-catalyzed asymmetric epoxidation of allylic alcohols as well as homoallylic alcohols. From this success we demonstrate the versatile nature of BHA in the molybdenum catalyzed asymmetric oxidation of unfunctionalized olefins and sulfides.
