111466-55-8Relevant academic research and scientific papers
Total stereocontrolled synthesis of a novel pyrrolizidine iminosugar
De Angelis, Martina,Primitivo, Ludovica,Lizzio, Federica,Agostinelli, Sonia,Sappino, Carla,Ben Romdan, Ilaria,Bonanni, Luciano,D'Annibale, Andrea,Antonioletti, Roberto,Ricelli, Alessandra,Righi, Giuliana
, (2021/12/20)
Herein we describe a versatile approach to the pyrrolizidine alkaloids skeleton by tailoring our original strategy already used for the pyrrolidine iminosugars synthesis. The key steps are the regio- and stereoselective azidolysis of the suitable chiral v
An efficient stereoselective total synthesis of 11β-methoxycurvularin
Yadav,Vani, C. Divya,Bhasker,Reddy, B.V. Subba
, p. 291 - 300 (2014/10/15)
A very short and efficient stereoselective total synthesis of a macrocyclic ketone, 11β-methoxycurvularin was achieved by employing the Sharpless asymmetric epoxidation, formation of propargyl alcohols from an epoxy-chloride, and intramolecular Friedel-Cr
Enantioselective synthesis of the natural product (S)-rugulactone
Nagaiah, Burea,Narsaiah, Akkirala Venkat
, p. 1948 - 1954 (2013/11/06)
A simple and efficient enantioselective synthesis of (6S)-5,6-dihydro-6- [(2E)-4-oxo-6-phenylhex-2-en-1-yl]-2H-pyran-2-one (=(S)-rugulactone) has been accomplished. The synthesis started from commercially available propane-1,3-diol and ethyl 3-phenylpropa
Synthesis of the FG ring fragment of pectenotoxins 1-9
Heapy, Amanda M.,Brimble, Margaret A.
scheme or table, p. 5424 - 5431 (2010/08/13)
The synthesis of the FG ring fragment common to pectenotoxins 1-9 is reported.The successful, convergent synthesis relied on high yielding routes to access two key intermediates; aldehyde 1 and phosphonium salt 2.A Z-selective Wittig reaction gave access
Synthesis of the FG fragment of the pectenotoxins
Heapy, Amanda M.,Wagner, Thomas W.,Brimble, Margaret M.
, p. 2359 - 2362 (2008/03/13)
The synthesis of the FG subunit of the pectenotoxins is reported herein. The synthesis hinges on the preparation of an appropriately functionalized acyclic precursor using a Z-selective Wittig reaction. Further elaboration using two sequential cyclization
Synthesis of diastereomerically and enantiomerically pure 2,3-disubstituted tetrahydrofurans using a sulfoxonium ylide
Schomaker, Jennifer M.,Pulgam, Veera Reddy,Borhan, Babak
, p. 13600 - 13601 (2007/10/03)
Nucleophilic substitution reactions of 2,3-epoxy alcohols, easily prepared via Sharpless asymmetric epoxidation chemistry, offer access to a wide variety of enantiomerically pure compounds. In this communication, we describe the use of a Payne rearrangement to control regioselectivity in the ring-opening of a series of 2,3-epoxy alcohols with dimethylsulfoxonium methylide to yield diastereomerically and/or enantiomerically pure disubstituted tetrahydrofuran rings. The factors influencing the success and substitution pattern of the THF ring products are discussed, including steric, electronic, and solvent effects. Copyright
Enantio- and stereocontrolled formation of the bisspiroacetal core of spirolide B
Ishihara, Jun,Ishizaka, Tomoko,Suzuki, Takanori,Hatakeyama, Susumi
, p. 7855 - 7858 (2007/10/03)
The bisspiroacetal core of spirolide B, a marine natural toxin, was synthesized from triketone 10 via one-step bisspiroacetalization, methylation, and silylation accompanied by isomerization of the C-15 spirocenter. The equilibrium of two isomers under ac
Indium mediated efficient conversion of 2-iodomethyl aziridines to chiral allylic amines
Yadav,Bandyopadhyay,Reddy
, p. 1608 - 1610 (2007/10/03)
Chiral allylic amines are synthesized in high yields by treatment of 2-iodomethyl N-tosyl aziridines with metallic indium in methanol at reflux.
A total synthesis of the unique tris-oxazole macrolide ulapualide a produced by the marine nudibranch Hexabranchus sanguineus
Chattopadhyay, Shital K.,Pattenden, Gerald
, p. 2429 - 2454 (2007/10/03)
A total synthesis of ulapualide A (1), whose relative stereochemistry was assigned on the basis of an earlier molecular mechanics study of its hypothetical metal chelated complex 9, is described. The synthesis is based on: i, elaboration of the double fun
Synthetic studies towards novel tris-oxazole based macrolides of marine origin. Stereocontrolled synthesis of the C20 - C35 fragment in ulapualide A
Chattopadhyay, Shital K.,Pattenden, Gerald
, p. 5271 - 5274 (2007/10/02)
The C20 - C35 subunit 3 in ulapualide A 1 has been synthesised in enantiomerically pure form using a combination of the Evans aldol reaction, controlled ring opening reactions of chiral epoxides, and Brown's asymmetric allylboration reaction, to set up th
