109856-84-0Relevant articles and documents
Organocatalytic enantioselective synthesis of 1,3,5-polyols by means of iterative asymmetric epoxidation: Their application to the total synthesis of polyrhacitide A
Kumaraswamy, Gullapalli,Murthy, Akula Narayana,Sadaiah, Kadivendi
, p. 3179 - 3186 (2012)
We have developed a pragmatic route to the stereogenic skipped 1,3,5-polyols. The strategic transformation includes an organocatalytic enantioselective asymmetric epoxidation, which is either syn- or anti-selective as genesis of chirality and successive SN2 opening reaction by an appropriate functionalized nucleophile, followed by hydroboration/oxidation to generate stereoisomers in good yield. The critical intermediate generated en route to this process is employed in the total synthesis of polyrhacitide A.
A chemical of pharmaceutical intermediate preparation method
-
Paragraph 0031-0032, (2019/07/01)
The invention discloses a chemical of pharmaceutical intermediate preparation method, its chemical name: (2R) - 1 - [(4S, 5R) - 4 - (2, 2 - Dimethyl - 5 - vinyl - 1, 3 - cyclo pentyl)] - 2 - nonanol, which belongs to the field of chemical pharmaceutical intermediates. The invention from chiral material (S)- ech start, preparation process requires through Grignard reaction, reduction reaction, the cyclization reaction prins, asymmetric double-hydroxylation reaction, such as zinc powder in the elimination reaction of the 9 step reaction. The invention has simple operation, the raw material is cheap, novel synthetic route, efficient construction chiral central and the like.
Method for preparing pharmaceutical intermediate
-
Paragraph 0024; 0031-0032, (2019/11/20)
The invention discloses a method for preparing a pharmaceutical intermediate, and belongs to the field of chemical pharmaceutical intermediates. The chemical name of the pharmaceutical intermediate is(2R)-1-[(4S,5R)-4-(2,2-dimethyl-5-vinyl-1,3-dioxolane)]-2-nonyl alcohol. According to the method for preparing the pharmaceutical intermediate, starting from a chiral raw material (S)-epoxy chloropropane, the preparation process includes 9 reaction steps such as Grignard reaction, reduction reaction, prins cyclization reaction, asymmetric dihydroxylation reaction and elimination reaction which involves zinc powder. The method for preparing the pharmaceutical intermediate has the advantages of simple operation, low-cost easily-obtained raw materials, a novel synthesis route, efficient construction of multiple chiral centers and the like.
Synthesis and Absolute Configuration of Two Natural Phenolic Homobenzyl Esters
Xu, Murong,Zhu, Shijun,Xu, Zejun,Wu, Yikang,Gao, Po
, p. 729 - 738 (2015/12/05)
Two recently identified natural phenolic homobenzyl esters, isolated from Phragmipedium calurum (an orchid) and Eupatorium fortunei TURCZ (a perennial herb in the Asteraceae family), respectively, were synthesized in enantiopure forms. By comparison of the optical rotations for the synthetic and the natural samples, the absolute configurations for the natural products were reliably assigned. The synthesis also enables establishment of the absolute configuration of a closely related natural homobenzyl alcohol and provided for the first time complete physical and spectroscopic data for two other natural homobenzyl esters. Two recently isolated natural phenolic homobenzyl esters were synthesized in enantiopure forms. The absolute configurations for these natural products were thus reliably assigned. En route to the total synthesis of the first target, complete physical and spectroscopic data for two other related natural products were made available for the first time. Configuration assignment of a third natural product was also achieved.
First total synthesis of achaetolide
Chandrasekhar,Balaji,Rajesh
scheme or table, p. 5164 - 5166 (2010/11/16)
The first total synthesis of achaetolide, a 10-membered macrolactone was achieved using Mitsunobu reaction and Grubbs ring-closing metathesis reaction as the key steps for ring construction. The desired stereo centres were generated by Jacobsen hydrolytic kinetic resolution, dihydroxylation and Sharpless asymmetric epoxidation reactions.
Stereocontrol of 5,5-spiroketals in the synthesis of cephalosporolide H epimers
Tlais, Sami F.,Dudley, Gregory B.
supporting information; experimental part, p. 4698 - 4701 (2011/01/12)
A blueprint for controlling the stereochemistry of oxygenated 5,5-spiroketals using chelation effects is provided. Chelation specifically of zinc salts (other protic and Lewis acids were less effective) between the spiroketal oxygen and an appropriately positioned alcohol group overrides normal biases in the preparation of 5,5-spiroketals, as illustrated by the stereocontrolled synthesis of epimeric cephalosporolide H isomers. This study provides new and valuable information for prescribing the chirality of the stereogenic core of 5,5-spiroketals.
Rhodium catalysed conjugate addition of a chiral alkenyltrifluoroborate salt: The enantioselective synthesis of hermitamides A and B
Frost, Christopher G.,Penrose, Stephen D.,Gleave, Robert
experimental part, p. 4340 - 4347 (2009/02/07)
The concise enantioselective synthesis of hermitamides A and B is presented utilising a rhodium catalysed conjugate addition reaction to introduce the side chain and chiral information in a single step via an alkenyltrifluoroborate salt.
Total synthesis of malyngamide X and its 7′S-epi isomer
Suntornchashwej, Suchada,Suwanborirux, Khanit,Isobe, Minoru
, p. 3217 - 3226 (2007/10/03)
Stereoselective syntheses of malyngamide X (1) and its 7′(S)-epimer are described. A Lewis acid (Et2AlCl) mediated anti-aldol reaction was employed to generate the stereocenters C-7 and C-8. The route is convergent and provides a convenient acc
Asymmetric synthesis of 3-substituted 3,4-dihydroisocoumarins via stereoselective addition of laterally lithiated chiral 2-(o-tolyl)oxazolines to aldehydes followed by diastereomer-selective lactonization
Kurosaki, Yuji,Fukuda, Tsutomu,Iwao, Masatomo
, p. 3289 - 3303 (2007/10/03)
Lateral lithiation of (S)-4-isopropyl-2-(o-tolyl)oxazoline in diethyl ether followed by the reaction with aldehydes in the presence of TMEDA produced the addition products with stereoselectivities up to 84% de. Utilization of TMEDA as a ligand is essential for the good selectivity. Rationale for the stereoselectivity is proposed based on ab initio calculation of the lateral lithio species. The major (S,S)-products lactonized faster than the minor (S,R)-products to the corresponding 3,4-dihydroisocoumarins under acidic conditions. Thus, (3S)-3,4-dihydroisocoumarins were obtained in good optical purities up to 97% ee by sequential application of these matched stereoselective reactions.
Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors
Kim, Choung U.,Lew, Willard,Williams, Matthew A.,Wu, Huiwei,Zhang, Lijun,Chen, Xiaowu,Escarpe, Paul A.,Mendel, Dirk B.,Laver, W. Graeme,Stevens, Raymond C.
, p. 2451 - 2460 (2007/10/03)
A series of influenza neuraminidase inhibitors with the cyclohexene scaffold containing lipophilic side chains have been synthesized and evaluated for influenza A and B neuraminidase inhibitory activity. The size and geometry of side chains have been modified systematically in order to investigate structure-activity relationships of this class of compounds. The X-ray crystal structures of several analogues complexed with neuraminidase revealed that the lipophilic side chains bound to the hydrophobic pocket consisted of Glu276, Ala246, Arg224, and Ile222 of the enzyme active site. The structure-activity relationship studies of this series have also demonstrated remarkably different inhibitory potency between influenza A and B neuraminidase. This indicated that the lipophilic side chains had quite different hydrophobic interactions with influenza A and B neuraminidase despite their complete homology in the active site. Influenza B neuraminidase appeared to be much more sensitive toward the increased steric bulkiness of inhibitors compared to influenza A neuraminidase. From the extensive structure-activity relationship investigation reported in this article, GS 4071 emerged as one of the most potent influenza neuraminidase inhibitors against both influenza A and B strains.
