131375-63-8Relevant academic research and scientific papers
Total synthesis of (+)-rubriflordilactone A
Goh, Shermin S.,Chaubet, Guilhem,Gockel, Birgit,Cordonnier, Marie-Caroline A.,Baars, Hannah,Phillips, Andrew W.,Anderson, Edward A.
, p. 12618 - 12621 (2015)
Two enantioselective total syntheses of the nortriterpenoid natural product rubriflordilactone A are described, which use palladium- or cobalt-catalyzed cyclizations to form the CDE rings, and converge on a late-stage synthetic intermediate. These key processes are set up through the convergent coupling of a common diyne component with appropriate AB-ring aldehydes, a strategy that sets the stage for the synthetic exploration of other members of this family of natural products. Two in one: Two enantioselective total syntheses of the nortriterpenoid natural product rubriflordilactone A are described, which use palladium- or cobalt-catalyzed cyclizations to converge on a late-stage synthetic intermediate. These key processes are set up through the coupling of a common diyne component with appropriate AB-ring aldehydes, a strategy that enables a broad exploration of this family of natural products, as well as synthetic analogues.
Synthesis of the polyketide moiety of the jamaicamides
Tanaka-Yanuma, Ayano,Watanabe, Satoshi,Ogawa, Keita,Watanabe, Sho,Aoki, Naoto,Ogura, Tetsuhiro,Usuki, Toyonobu
, p. 6777 - 6781 (2015)
[Figure presented] Isolated from the Jamaican cyanobacterium Lyngbya majuscula, the jamaicamides are unique, mixed polyketide-peptides reported to be sodium channel blockers. The polyketide moiety contains an (E)-chloroolefin, an undetermined methyl stere
Regioselective Preparation of Fullerene Bis-adducts from Cleavable Macrocyclic Bis-malonates
Trinh, Thi Minh Nguyet,Schillinger, Franck,Guerra, Sebastiano,Meichsner, Eric,Nierengarten, Iwona,Hahn, Uwe,Holler, Michel,Nierengarten, Jean-Fran?ois
, p. 3770 - 3786 (2021/06/27)
A series of macrocyclic bis-malonates incorporating either di-tert-butylsilylene or tetra-iso-propyldisiloxane subunits have been prepared and used for the regioselective bis-functionalization of [60]fullerene by double Bingel cyclopropanations. By system
Modular Fragment Synthesis and Bioinformatic Analysis Propose a Revised Vancoresmycin Stereoconfiguration
Adamek, Martina,Essig, Sebastian,Kurz, Michael,Menche, Dirk,Sch?nenbroicher, Max,Seul, Maximilian,Spindler, Stefanie,Wingen, Lukas M.,Ziemert, Nadine
supporting information, p. 1175 - 1180 (2021/01/13)
Elaborate fragments of the proposed stereostructure of the complex polyketide antibiotic vancoresmycin have been synthesized in a stereoselective fashion based on a modular and convergent approach. Significant nuclear magnetic resonance differences in one of these subunits compared with the natural product question the proposed stereoconfiguration. Consequently, an extensive bioinformatics analysis of the biosynthetic gene cluster was carried out, leading to a revised stereoconfigurational proposal for this highly potent antibiotic.
Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)3
Hoshino, Yoshihiko,Iwabuchi, Yoshiharu,Kuriyama, Yuse,Sasano, Yusuke,Uesugi, Shun-ichiro,Yamaichi, Aoto
supporting information, p. 1961 - 1965 (2021/01/04)
Highly regioselective intramolecular aminolysis of 3,4-epoxy amines has been achieved. Key features of this reaction are (1) chemoselective activation of epoxides in the presence of unprotected aliphatic amines in the same molecules by a La(OTf)3 catalyst and (2) excellent regioselectivity for anti-Baldwin 5-endo-tet cyclization. This reaction affords 3-hydroxy-2-alkylpyrrolidines stereospecifically in high yields. DFT calculations revealed that the regioselectivity might be attributed to distortion energies of epoxy amine substrates. The use of this reaction was demonstrated by the first enantioselective synthesis of an antispasmodic agent prifinium bromide.
Diastereoselective and Branched-Aldehyde-Selective Tandem Hydroformylation-Hemiaminal Formation: Synthesis of Functionalized Piperidines and Amino Alcohols
Pittaway, Rachael,Fuentes, José A.,Clarke, Matthew L.
, p. 2845 - 2848 (2017/06/07)
Starting from readily available allylglycine, a tandem hydroformylation-hemiaminal formation reaction has been developed for the synthesis of chiral functionalized piperidines, with very good diastereoselectivity and branched regioselectivity using Rh/(S,
Fluorinated Musk Fragrances: The CF2Group as a Conformational Bias Influencing the Odour of Civetone and (R)-Muscone
Callejo, Ricardo,Corr, Michael J.,Yang, Mingyan,Wang, Mingan,Cordes, David B.,Slawin, Alexandra M. Z.,O'Hagan, David
, p. 8137 - 8151 (2016/06/13)
The difluoromethylene (CF2) group has a strong tendency to adopt corner over edge locations in aliphatic macrocycles. In this study, the CF2group has been introduced into musk relevant macrocyclic ketones. Nine civetone and five muscone analogues have been prepared by synthesis for structure and odour comparisons. X-ray studies indeed show that the CF2groups influence ring structure and they give some insight into the preferred ring conformations, triggering a musk odour as determined in a professional perfumery environment. The historical conformational model of Bersuker and co-workers for musk fragrance generally holds, and structures that become distorted from this consensus, by the particular placement of the CF2groups, lose their musk fragrance and become less pleasant.
Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12
Egger, Julian,Fischer, Stefan,Bretscher, Peter,Freigang, Stefan,Kopf, Manfred,Carreira, Erick M.
supporting information, p. 4340 - 4343 (2015/09/15)
An efficient synthesis of 15-deoxy-Δ12,14-prostaglandin J2 (15d-PGJ2, 1) is reported. The route described allows for diversification of the parent structure to prepare seven analogues of 1 in which the positioning of electrophilic sites is varied. These analogues were tested in SAR studies for their ability to reduce the secretion of proinflammatory cytokines. It was shown that the endocyclic enone is crucial for the bioactivity investigated and that the conjugated ω-side chain serves in a reinforcing manner.
SYNTHESIS OF DELTA 12-PGJ3 AND RELATED COMPOUNDS
-
Page/Page column 94; 95, (2015/04/15)
In one aspect, the present invention provides novel derivatives of Δ12-PGJ3 and modular synthetic pathways to obtaining Δ12-PGJ3 and derivatives thereof. In some aspects, the present derivatives of Δ12-PGJ3 are useful as chemotherapeutic agents. The present disclosure also describes compositions of these derivatives as well as methods of use of the derivatives thereof.
Fluorine in fragrances: Exploring the difluoromethylene (CF2) group as a conformational constraint in macrocyclic musk lactones
Corr, Michael J.,Cormanich, Rodrigo A.,Von Hahmann, Cortney N.,Bühl, Michael,Cordes, David B.,Slawin, Alexandra M. Z.,O'Hagan, David
supporting information, p. 211 - 219 (2015/12/30)
The CF2 group is incorporated into specific positions within the lactone ring of the natural musk lactone, (12R)-(+)-12-methyl-13-tridecanolide, a constituent of Angelica root oil, Angelica archangelica L. The approach is taken as it was antici
