92817-88-4Relevant academic research and scientific papers
Stereochemically versatile synthesis of the C1-C12 fragment of tedanolide c
Smith, Thomas E.,Fink, Sarah J.,Levine, Zebulon G.,McClelland, Kerani A.,Zackheim, Adrian A.,Daub, Mary E.
, p. 1452 - 1455 (2012)
A flexible synthesis of the C1-C12 fragment of Tedanolide C has been accomplished in eight steps from 2-methyl-2,4-pentadienal. Asymmetric hydroformylation of a 1,3-diene allows for the late-stage generation of either C10 epimer with complete catalyst con
Identification and Total Synthesis of an Unstable Anticancer Macrolide Presaccharothriolide Z Produced by Saccharothrix sp. A1506
Ikeda, Hiroaki,Kakeya, Hideaki,Kuranaga, Takefumi,Nakagawa, Yusuke,Tamura, Miho,Terada, Sakahiro
, p. 7106 - 7111 (2021/09/14)
Saccharothriolides A-F are 10-membered microbial macrolides proposed to be generated from their precursors presaccharothriolides X-Z. Previously, we isolated presaccharothriolide X, and its unique natural prodrug-like properties have intrigued us. However
Syntheses of Gymnothespirolignans B and C and Non-natural Isomer 9-Epi-gymnothespirolignan B
Ali, Ghada,Cuny, Gregory D.
, p. 10517 - 10525 (2021/07/31)
Syntheses of polycyclic spiro lignans gymnothespirolignans B and C as well as the unnatural isomer 9-epi-gymnothespirolignan B were accomplished using (R)-Roche ester and an appropriately substituted fluorenone. Key features of the convergent syntheses include coupling of the fluorenone and an iodo-alkene intermediate derived from (R)-Roche ester in the presence of the Lewis acid TiCl(OiPr)3, C9-O bond formation via an SN2 reaction with retention of stereochemistry, and diastereoselective hydrogenations of a common alkene intermediate guided by accessibility or positioning by the C8-methoxy.
The discovery and evaluation of 3-amino-2(1H)-pyrazinones as a novel series of selective p38α MAP kinase inhibitors
Evans, Richard,Raubo, Piotr,Willis, Paul
, (2020/07/21)
The discovery and optimisation of a novel series of potent and selective p38α inhibitors is described. Evaluating the structure-activity relationship of an aminoalkyl substituent at the 3 position of the 2(1H)-pyrazinone core, p38α potency was increased 20000-fold. The most advanced compound (25) demonstrated excellent in vivo properties suitable for an inhaled route of administration.
Ring-closing metathesis approaches towards the total synthesis of rhizoxins
Altmann, Karl-Heinz,Liniger, Marc,Neuhaus, Christian M.
supporting information, (2020/10/18)
Efforts are described towards the total synthesis of the bacterial macrolide rhizoxin F, which is a potent tubulin assembly and cancer cell growth inhibitor. A significant amount of work was expanded on the construction of the rhizoxin core macrocycle by ring-closing olefin metathesis (RCM) between C(9) and C(10), either directly or by using relay substrates, but in no case was ringclosure achieved. Macrocycle formation was possible by ring-closing alkyne metathesis (RCAM) at the C(9)/C(10) site. The requisite diyne was obtained from advanced intermediates that had been prepared as part of the synthesis of the RCM substrates. While the direct conversion of the triple bond formed in the ring-closing step into the C(9)-C(10) E double bond of the rhizoxin macrocycle proved to be elusive, the corresponding Z isomer was accessible with high selectivity by reductive decomplexation of the biscobalt hexacarbonyl complex of the triple bond with ethylpiperidinium hypophosphite. Radical-induced double bond isomerization, full elaboration of the C(15) side chain, and directed epoxidation of the C(11)-C(12) double bond completed the total synthesis of rhizoxin F.
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
Polyoxygenated Tertiary Alcohols: A Kiyooka Approach
Lücke, Daniel,Kalesse, Markus
, p. 10080 - 10083 (2019/07/18)
A Kiyooka aldol approach for the stereoselective synthesis of tertiary alcohols is presented. This approach allows for the incorporation of different substituents at all three remaining positions at the chiral center bearing the tertiary alcohol. To demon
Electrochemical and photochemical approaches for the synthesis of the C28–C38 fragment of okadaic acid
Dochain, Simon,Nshimyumuremyi, Jean-Boris,Dewez, Damien F.,Body, Jean-Fran?ois,Elias, Benjamin,Singleton, Michael L.,Markó, István E.
, p. 2280 - 2283 (2019/03/06)
Okadaic acid, a potent and selective inhibitor of Protein Phosphatases 1 and 2A (PP1 and PP2A), is widely used as a probe for various biochemical processes. We describe herein two innovative methods for the synthesis of the terminal C28–C38 fragment of the natural polyether. Suárez photochemical oxidative cyclization and electrochemical oxidation of malonates to their ketals equivalents have been successfully applied for the assembly of the key spiroketal core.
(R)-N-(1-Methyl-2-hydroxyethyl)-13-(S)-methyl-arachidonamide (AMG315): A Novel Chiral Potent Endocannabinoid Ligand with Stability to Metabolizing Enzymes
Liu, Yingpeng,Ji, Lipin,Eno, Marsha,Kudalkar, Shalley,Li, Ai-Ling,Schimpgen, Marion,Benchama, Othman,Morales, Paula,Xu, Shu,Hurst, Dow,Wu, Simiao,Mohammad, Khadijah A.,Wood, Jodianne T.,Zvonok, Nikolai,Papahatjis, Demetris P.,Zhou, Han,Honrao, Chandrashekhar,MacKie, Ken,Reggio, Patricia,Hohmann, Andrea G.,Marnett, Lawrence J.,Makriyannis, Alexandros,Nikas, Spyros P.
, p. 8639 - 8657 (2018/10/02)
The synthesis of potent metabolically stable endocannabinoids is challenging. Here we report a chiral arachidonoyl ethanolamide (AEA) analogue, namely, (13S,1′R)-dimethylanandamide (AMG315, 3a), a high affinity ligand for the CB1 receptor (Ki o
Stereoselective synthesis of the C3-C15 fragment of callyspongiolide
Reddy Ramidi, Gopal,Yadav, Jhillu S.,Mohapatra, Debendra K.
supporting information, p. 3579 - 3582 (2018/09/10)
The synthesis of C3-C15 fragment of callyspongiolide, a 14-membered macrolides isolated from the marine sponge Callyspongia sp., which was collected from the Indonesia, is reported. Highlights of the synthesis include construction of E-olefin through Juli
