80910-01-6Relevant articles and documents
Total Synthesis of Kalimantacin A
Davies, Jonathan A.,Bull, Freya M.,Walker, Paul D.,Weir, Angus N. M.,Lavigne, Rob,Masschelein, Joleen,Simpson, Thomas J.,Race, Paul R.,Crump, Matthew P.,Willis, Christine L.
supporting information, p. 6349 - 6353 (2020/09/02)
The kalimantacins make up a family of hybrid polyketide-nonribosomal peptide-derived natural products that display potent and selective antibiotic activity against multidrug resistant strains of Staphylococcus aureus. Herein, we report the first total synthesis of kalimantacin A, in which three fragments are prepared and then united via Sonogashira and amide couplings. The enantioselective synthetic approach is convergent, unlocking routes to further kalimantacins and analogues for structure-activity relationship studies and clinical evaluation.
A Method for the Stereoselective Construction of the Hemiaminal Center in Zampanolides
Brütsch, Tobias M.,Berardozzi, Simone,Rothe, Marlene L.,Horcajo, Mariano Redondo,Diáz, José Fernando,Altmann, Karl-Heinz
supporting information, p. 8345 - 8348 (2020/11/03)
We have developed a new method for the stereoselective establishment of the N-acyl hemiaminal moiety in zampanolide-type structures that involves the reaction of (Z,E)-sorbamide (3) with BINAL-H and subsequent amide transfer from a putative aluminum carbo
A Synthesis Strategy for the Production of a Macrolactone of Gulmirecin A via a Ni(0)-Mediated Reductive Cyclization Reaction
Ichikawa, Satoshi,Katsuyama, Akira,Kitahata, Shun
supporting information, (2020/03/30)
A synthesis strategy for the production of a key synthetic intermediate of gulmirecin A was described. The key reaction in the preparation of the 12-membered macrolactone is the Ni(0)-mediated reductive cyclization reaction of ynal using an N-heterocyclic carbene ligand and silane reductant. In addition, the α-selective glycosylation reaction of the macrolactone was performed to demonstrate the synthesis of gulmirecin and disciformycin precursors.
Exploration of the structure–activity relationship and druggability of novel oxazolidinone-based compounds as Gram-negative antibacterial agents
Ding, Shi,Ji, Jing-Chao,Zhang, Ming-Juan,Yang, Yu-She,Wang, Rui,Zhu, Xing-Long,Wang, Li-Hong,Zhong, Yi,Gao, Le,Lu, Man,Liu, Ju,Chen, Ye
, (2019/09/06)
To gain further knowledge of the structure–activity relationship and druggability of novel oxazolidinone-based UDP-3-O-acyl-N-acetylglucosamine deacetylase (LpxC) inhibitors as Gram-negative antibacterial agents, compounds containing the hydrophobic tails
Organozinc-aided, HMPA-free, stoichiometric three-component coupling for the general synthesis of prostaglandins and stable prostacyclin analogs with biological significance
Koyama, Hiroko,Izumiseki, Atsuto,Suzuki, Masaaki
, p. 1467 - 1470 (2019/05/07)
A three-component coupling procedure was developed to construct the entire prostaglandin (PG) skeleton under HMPA-free and stoichiometric conditions via a combination of dimethylzinc-aided conjugate addition of an ω-side-chain vinyllithium with (R)-4-hydroxy-2-cyclopentenone and the direct trapping of the resulting enolate with an α-side-chain propargyl triflate. Dimethylzinc effectively regulated both the conjugate addition and alkynylation reactions. Thus, the method afforded protected 5,6-didehydro-PGE2, a common intermediate for the general synthesis of natural PGs and the stable artificial prostacyclin (PGI2) analog isocarbacyclin in 88% yield. The utility of the method was further applied to the syntheses of novel intermediates, which are useful for the straightforward synthesis of 15R-TIC and 15-deoxy-TIC in 79% and 86% yield, respectively.
Synthesis, conformational preferences, and biological activity of conformational analogues of the microtubule-stabilizing agents, (-)-zampanolide and (-)-dactylolide
Henry, Jeffrey L.,Wilson, Matthew R.,Mulligan, Michael P.,Quinn, Taylor R.,Sackett, Dan L.,Taylor, Richard E.
supporting information, p. 800 - 805 (2019/05/29)
Zampanolide and dactylolide are microtubule-stabilizing polyketides possessing potent cytotoxicity towards a variety of cancer cell lines. Using our understanding of the conformational preferences of the macrolide core in both natural products, we hypothe
Stereoselective Synthesis of the C1-C22 Carbon Framework of (-)-Amphidinolide K
Chandankar, Somnath S.,Raghavan, Sadagopan
, p. 9584 - 9602 (2019/09/06)
Two stereoselective routes to the C7-C22 subunit of amphidinolide K are disclosed. Jacobsen's hydrolytic kinetic resolution and Sharpless' asymmetric dihydroxylation reactions have been employed for the construction of the tetrahydrofuran ring. The C10-C1
Total Synthesis of Belizentrin Methyl Ester: Report on a Likely Conquest
Anderl, Felix,Gr??l, Sylvester,Wirtz, Conny,Fürstner, Alois
supporting information, p. 10712 - 10717 (2018/08/17)
The assigned structure of the dinoflagellate-derived toxin belizentrin was prepared by total synthesis in form of the corresponding methyl ester for stability reasons. The successful route features an unusual solution for the preparation of a recalcitrant ylide on a C-glycosidic segment; moreover, it involves an asymmetric hetero-Diels–Alder reaction en route to the tertiary hemiacetal substructure, a Negishi cross-coupling of two elaborate building blocks, and a macrocyclization based on an intramolecular aminolysis of a spirolactone. A modified Kocienski olefination ultimately allowed the polyol side chain to be attached to the macrocycle although this transformation faced the exceptional base sensitivity of this polyunsaturated target compound.
Two simple and alternative approaches for the synthesis of anticancer active goniothalamin
Narasimhulu, Manchala,Siva Prasad,Appa, Rama Moorthy,Lakshmidevi, Jangam,Venkateswarlu, Katta
, p. 326 - 337 (2018/07/05)
Two alternative and straightforward routes were developed for the construction of (R)-goniothalamin, a natural anticancer agent. The first method starts with (R)-glycidol involving stereoselective (partial) reduction of alkyne and sulfoxide Julia-Lythgoe
Total Synthesis and Biological Activity of the Arachidonic Acid Metabolite Hemiketal E2
Boer, Robert E.,Giménez-Bastida, Juan Antonio,Boutaud, Olivier,Jana, Somnath,Schneider, Claus,Sulikowski, Gary A.
, p. 4020 - 4022 (2018/07/15)
The total synthesis of hemiketal E2 (HKE2) has been accomplished using a gold(I)-mediated cycloisomerization followed by oxidation of the enol ether product to introduce a unique keto-hemiketal, the core structure of HKE2.
