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
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
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
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
