131375-69-4Relevant academic research and scientific papers
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.
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.
Observations on the Influence of Precursor Conformations on Macrocyclization Reactions
Hammersh?j, Peter,Beldring, Klavs,Nielsen, Anders R.,Fristrup, Peter,Clausen, Mads H.
supporting information, p. 1533 - 1540 (2016/04/05)
Macrocycles hold great promise in drug discovery as an underutilized class of lead compounds. The low abundance of these molecules can, in part, be explained by the inherent difficulties in the synthesis of macrocycles and the lack of general methods for their rapid assembly. We have undertaken a research program aimed at developing methods for facile synthesis of macrocycles from simple precursors. The synthesis of two new cyclization precursors is described and the results of their reaction with thionyl chloride are presented and discussed. Whereas one acyclic diol smoothly underwent macrocyclization to afford a mixture of diastereomeric sulfites, subjection of the other precursor to identical reaction conditions resulted in the isolation of the linear dichloride. We hypothesize that there is a difference in the ability of the two molecules to adopt a conformation that is germane to macrocyclization, a proposition that is supported by conformational analyses using molecular mechanics. Macrocycles hold great promise in drug discovery; however, their synthetic generation through macrocyclization is nontrivial. Here, the synthesis of two new cyclization precursors is described and the results of the ensuing cyclization is reported and evaluated. Molecular modeling is used to explain the observed results and provide guidance for further work in this field.
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
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 the polyketide moiety of the jamaicamides
Tanaka-Yanuma, Ayano,Watanabe, Satoshi,Ogawa, Keita,Watanabe, Sho,Aoki, Naoto,Ogura, Tetsuhiro,Usuki, Toyonobu
supporting information, p. 6777 - 6781 (2018/05/14)
[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
Bisnucleophilic substitution as a synthetic tool for ready access to the piperidine alkaloids (+)-Connine, (+)-β-conhydrine, (+)-8-ethylnorlobelol, and (-)-halosaline
Raju, Galla,Anitha, Kadimi,Krishna, Palakodety Radha
, p. 937 - 941 (2015/04/27)
Herein we report the stereoselective total synthesis of (+)-connine, (+)-β-conhydrine, (+)-8-ethylnorlobelol, and (-)-halosaline via bisnucleophilic substitution with benzylamine as the key step.
Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand
Yu, Zhiyong,Eno, Meredith S.,Annis, Alexandra H.,Morken, James P.
, p. 3264 - 3267 (2015/07/15)
A rhodium complex, in conjunction with commercially available Ph-BPE ligand, catalyzes the branch-selective asymmetric hydroformylation of 1-alkenes and rapidly generates α-chiral aldehydes. A wide range of terminal olefins including 1-dodecene were examined, and all delivered high enantioselectivity (up to 98:2 er) as well as good branch:linear ratios (up to 15:1). (Chemical Equation Presented).
Stereoselective Total Synthesis of psiAβ - A Sporogenic Psi Factor from Aspergillus nidulans 1
Reddy, Parigi Raghavendar,Lingaiah, Maram,Das, Biswanath
, p. 975 - 976 (2014/05/06)
The stereoselective total synthesis of psiAβ, a sporogenic psi factor of the fungus Aspergillus nidulans, has been accomplished starting from pentane-1,5-diol. The synthesis involves an enantioselective Keck allylation, an asymmetric alkynylzinc addition,
