74141-13-2Relevant academic research and scientific papers
Substituted Tetraethynylethylene–Tetravinylethylene Hybrids
Connor, Kieran P. E.,Horvath, Kelsey L.,Magann, Nicholas L.,Sherburn, Michael S.,Sowden, Madison J.,Westley, Erin
supporting information, p. 977 - 986 (2022/02/03)
A general synthetic approach to molecular structures that are hybrids of tetraethynylethylene (TEE) and tetravinylethylene (TVE) is reported. The synthesis permits the controlled preparation of many previously inaccessible structures, including examples w
Synthesis of Optically Active N -(4-Hydroxynon-2-enyl)pyrrolidines: Key Building Blocks in the Total Synthesis of Streptomyces coelicolor Butanolide 5 (SCB-5) and Virginiae Butanolide A (VB-A)
Donges, Jonas,Hofmann, Sandra,Walter, Johannes C.,Reichertz, Julia,Brüggemann, Moritz,Frank, Andrea,Nubbemeyer, Udo
supporting information, p. 2632 - 2642 (2021/04/27)
Starting from 5-methylhexanal and (S)-configured N -propargylprolinol ethers, coupling delivered N -(4-hydroxynon-2-ynyl)prolinol derivatives as mixtures of C4 diastereomers. Resolution of the epimers succeeded after introduction of an (R)-mandelic ester derivative and subsequent HPLC separation. Alternatively, suitable oxidation gave the corresponding alkynyl ketone. Midland reagent controlled diastereoselective reduction afforded a defined configured propargyl alcohol with high selectivity. LiAlH 4reduction and Mosher analyses of the allyl alcohols enabled structure elucidation. The suitably protected products are used as key intermediates in enantioselective Streptomyces γ-butyrolactone signaling molecule total syntheses.
Enantioselective Total Synthesis of Cerorubenic Acid-III via Type II [5+2] Cycloaddition Reaction
Liu, Xin,Liu, Junyang,Wu, Jianlei,Li, Chuang-Chuang
, p. 11125 - 11139 (2021/05/29)
The first enantioselective total synthesis of cerorubenic acid-III is described in detail. Different strategies and attempts, based on a type II [5+2] cycloaddition reaction, leading to the bicyclo[4.4.1] ring system with a strained bridgehead double bond, are depicted. Furthermore, sodium naphthalenide was found to be efficient in the chemoselective reduction of 8-oxabicyclo[3.2.1]octene, with three transformations completed in one operation. An unusual SN1 transannular cyclization reaction was applied to construct the synthetically challenging vinylcyclopropane moiety. This strategy enabled the total synthesis of cerorubenic acid-III in 19 steps.
PROBE FOR DETECTING CARBAPENEM-RESISTANT BACTERIA AND USE THEREOF
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Paragraph 0085; 0099; 0100, (2021/09/10)
The present disclosure relates to a compound represented by Chemical Formula 1, a probe for detecting antibiotic-resistant bacteria, which includes the compound, a composition containing the compound, a kit including the compound and a method for detectin
DERIVATIVES OF THAILANSTATIN A, METHODS OF TREATMENT AND METHODS OF SYNTHESIS THEREOF
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Paragraph 0313, (2020/02/10)
In one aspect, the present disclosure provides analogs of thailanstatin of the formula wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein.
Synthesis of (Z)-alkene-containing linear conjugated dienyl homoallylic alcohols by a palladium-catalyzed three-component reaction
Horino, Yoshikazu,Sakamoto, Juri,Murakami, Miki,Sugata, Miki
supporting information, p. 1323 - 1327 (2020/08/21)
A synthesis of (Z)-alkene-containing linear conjugated dienyl homoallylic alcohols by using a palladium-catalyzed three-component reaction has been developed. This method shows good functional-group compatibility and generality, with high diastereoselectivity. Additionally, in many cases, the present method controls the alkene stereochemistry of the newly formed C-C bond and overcomes the inherent preference for (E)-alkene formation, giving (Z, E)- and (Z, Z)-products.
Synthesis of the C1-C12 Fragment of Calyculin C
Konstantinova, Olga V.,Koskinen, Ari M.P.
, p. 285 - 295 (2019/01/04)
Calyculins are a class of highly cytotoxic metabolites originally isolated from the marine sponge Discodermia calyx. To date, a total of twelve different calyculins (A-J) and calyculinamides (A, B and F) have been described, the most abundant (in D. calyx
Total Synthesis of Lajollamycin B
Nishimaru, Tatsuya,Eto, Kohei,Komine, Keita,Ishihara, Jun,Hatakeyama, Susumi
, p. 7927 - 7934 (2019/05/27)
The first total synthesis of lajollamycin B, a structurally novel nitro-tetraene spiro-β-lactone/γ-lactone antibiotic, is described. The convergent synthesis involves the construction of the C8′–C11′ nitrodienylstannane and its coupling with the segment prepared from the C1′–C7′ ω-iodoheptadienoic acid and the right-hand heterocyclic fragment, which has been utilized for our previous syntheses of oxazolomycin A. The revision of the geometry of the terminal Δ10′, 11′-double bond from E to Z is also described for the structure of natural lajollamycin B.
Versatile synthetic route to carbocyclic N-Acetylneuraminic acid and its derivatives
Mohan, Sankar,Thompson, John R.,Pinto, B. Mario,Bennet, Andrew J.
, p. 5213 - 5221 (2018/05/29)
Sialic acid (N-acetylneuraminic acid) is a carbohydrate that possess a nine carbon backbone, and it is often found at the termini of glycoconjugates in biological systems. Because of this prominence many syntheses have reported routes to sialic acid and m
Total Synthesis of the Marine Macrolide Amphidinolide F
Ferrié, Laurent,Fenneteau, Johan,Figadère, Bruno
supporting information, p. 3192 - 3196 (2018/06/11)
A new and efficient convergent approach toward the synthesis of amphidinolide F is described through the assembly of three fragments. The two trans-tetrahydrofurans were built by a diastereoselective C-glycosylation with titanium enolate of bulky N-acetyloxazolidinethiones. The side chain was inserted by a Liebeskind-Srogl cross-coupling reaction. A sulfone condensation/desulfonylation sequence, a Stille cross-coupling, and a macrolactonization were applied to connect the fragments.
