Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.201209112 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Stereoselective Synthesis of (±)-Tetraponerine-2 and -4 via the Gold(I)-Catalyzed Intramolecular Dehydrative Amination of Allylic Alcohols.
J Org Chem
December 2024
College of Pharmacy & Graduate School of Pharmaceutical Sciences, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-Gu, Seoul 03760, Republic of Korea.
The concise and efficient total synthesis of (±)-tetraponerine-2 () and (±)-tetraponerine-4 () was achieved in 9% and 14% overall yield, respectively. The key step included the diastereoselective gold(I)-catalyzed intramolecular dehydrative amination of an allylic alcohol-tethered sulfamide to produce the 1,3-diamine moiety. The resulting olefinic side chain was then elaborated by cross-metathesis and cyclized to a five-membered pyrrolidine or a six-membered piperidine ring by intramolecular Mitsunobu -alkylation.
View Article and Find Full Text PDFHydroxylamines: From Synthetic Intermediates to Synthetic Targets.
Acc Chem Res
October 2024
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore.
ConspectusSynergy between the teaching and research activities of a University should be a source of new ideas, each informing the other. A classroom discussion gave rise to our concept of using hydroxylamines as a form of "tethered nitrogen" for alkaloid synthesis. The "tether" temporarily connects a nucleophilic nitrogen atom to the substrate, rendering an intermolecular reaction intramolecular, thus providing stereo- and regiochemical control for C-N bond formation.
View Article and Find Full Text PDFStereoselective convergent total synthesis of oxylipins.
Org Biomol Chem
July 2024
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, Maharashtra, India.
We synthesized stereoselectively four stereoisomers of oxylipins (1a-d) by a convergent approach based on chiral catalysis. The synthetic approach involved sequential assembly of two key fragments - ene-diol and allyl alcohol - for an intended convergent cross-metathesis reaction to join these fragments. The key steps include Sharpless kinetic resolution, asymmetric dihydroxylation and Grubbs cross-metathesis.
View Article and Find Full Text PDFDesign and synthesis of 6-C-alkyl-DMDP type nanomolar inhibitors of β-galactosidase and β-glucosidase based on broussonetine S and related derivatives.
Eur J Med Chem
September 2024
Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China; University of Chinese Academy of Sciences, Beijing, 100049, China. Electronic address:
Broussonetine S (9), its C-1' and C-10' stereoisomers, and their corresponding enantiomers have been synthesized from enantiomeric arabinose-derived cyclic nitrones, with cross metathesis (CM), epoxidation and Keck asymmetric allylation as key steps. Glycosidase inhibition assays showed that broussonetine S (9) and its C-10' epimer (10'-epi-9) were nanomolar inhibitors of bovine liver β-galactosidase and β-glucosidase; while their C-1' stereoisomers were 10-fold less potent towards these enzymes. The glycosidase inhibition results and molecular docking calculations revealed the importance of the configurations of pyrrolidine core and C-1' hydroxyl for inhibition potency and spectra.
View Article and Find Full Text PDFStereoselective total synthesis of (3)- and (3)-elatenynes.
RSC Adv
December 2023
College of Pharmacy, Seoul National University Seoul 08826 Korea.
We describe here the highly stereoselective total synthesis of the C acetogenins (3)- and (3)-elatenynes having a 7,12-dibromo-6,9--10,13- adjacent bis-tetrahydrofuran (THF) core. The present synthesis features a highly stereoselective, protecting group-dependent, chelate-controlled intramolecular amide enolate alkylation (IAEA) for the synthesis of key intermediate 7-hydroxy-6,7--6,9--THF intermediate 10, deployment of the sequential ate complex (-BuLi/DIBAL-H) reduction/Keck allylation/cross metathesis (CM) protocol for the stereoselective introduction of the C(10)-C(15) unit, a sequential Sharpless asymmetric dihydroxylation (SAD)/intramolecular Williamson etherification for the construction of the 10,13--THF ring, and a modified Nakata chloromethanesulfonate-mediated S2 displacement for the 7,12-dibromo functionality. Furthermore, our strategy based on chelate-controlled IAEA methodology would provide access to any member of the C adjacent bis-THF acetogenin class.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!