We report an efficient Mukaiyama-aldol reaction of tryptanthrin with fluorinated enol silyl ethers, which is carried out in methanol without the use of any catalyst. This method is applied to the total synthesis of the difluoro analogues of the natural product Phaitanthrin B.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/c5ob01125f | DOI Listing |
In the fields of polymer and material chemistries, strong acid units have mainly included sulfonic acids, which has limited the extension of related material chemistries. Here, a unique carbon acid functionality, namely the bis[(trifluoromethyl)sulfonyl]methyl group, was integrated with polymers a simple postpolymerization modification with the outstandingly electrophilic 1,1-bis[(trifluoromethyl)sulfonyl]ethylene. The proposed synthesis protocol was verified as an efficient process even for solid-state reactions.
View Article and Find Full Text PDFOrg Biomol Chem
October 2024
School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, 1010, New Zealand.
Pallamolide A is a 7,8--labdane terpenoid possessing a unique bicyclo[2.2.2]octane core and a spiro-butenolide moiety.
View Article and Find Full Text PDFJ Org Chem
May 2024
CNRS, CiTCoM, Faculté de Pharmacie, Université Paris Cité, 4, avenue de l'Observatoire, F-75006 Paris, France.
In this paper are presented the results of the preliminary studies conducted on two model substrates that allowed the testing of various strategies and set the proper conditions that thereafter culminated in the synthesis of the C1-C23 chain of enacyloxin-IIa and its congeners. Innovative strategic options were explored on each model allowing the stereochemical control of the following two elements: (a) the 2, 4, 6, 8, and 10 chlorinated undecapentaenoic chain, thanks to -selective Kaneda's alkyne allylchlorination and an -selective Pd/Cu allene-alkyne coupling and (b) the unusual - -OH/-Cl/-OCONH 17-19 triad, thanks to a highly diastereoselective Mukaiyama aldol reaction.
View Article and Find Full Text PDFMolecules
April 2024
Bioorganic Chemistry Laboratory, Institut de Recherches Cliniques de Montréal (IRCM), Montréal, QC H2W 1R7, Canada.
The design of novel 4'-thionucleoside analogues bearing a C2' stereogenic all-carbon quaternary center is described. The synthesis involves a highly diastereoselective Mukaiyama aldol reaction, and a diastereoselective radical-based vinyl group transfer to generate the all-carbon stereogenic C2' center, along with different approaches to control the selectivity of the -glycosidic bond. Intramolecular S2-like cyclization of a mixture of acyclic thioaminals provided analogues with a pyrimidine nucleobase.
View Article and Find Full Text PDFJ Nat Prod
April 2024
School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, 920-1192, Japan.
PC-A (), a bromo nor-eremophilane, showed selective antiproliferative activity against a triple-negative breast cancer (TNBC) cell line. This unique activity prompted us to establish a total synthesis to facilitate a structure-activity relationship (SAR) study and selectivity optimization. An enantioselective first total synthesis of was achieved starting from ()-carvone through a side chain extension with a Mukaiyama aldol reaction and decalin construction.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!