156414-59-4Relevant academic research and scientific papers
Studies towards the total synthesis of rapamycin: Preparation of the cyclohexyl C33-C42 fragment and further coupling to afford the C22-C42 carbon unit
Kouklovsky,Ley,Marsden
, p. 2091 - 2094 (1994)
A short and stereoselective synthesis of the C33-C42 fragment 3 of rapamycin and its coupling with the previously prepared C22-C32 fragment 2 is described. The synthesis of 3 involves the preparation of enantiom
Total Synthesis of rapamycin
Ley, Steven V.,Tackett, Miles N.,Maddess, Matthew L.,Anderson, James C.,Brennan, Paul E.,Cappi, Michael W.,Heer, Jag P.,Helgen, Celine,Kori, Masakuni,Kouklovsky, Cyrille,Marsden, Stephen P.,Norman, Joanne,Osborn, David P.,Palomero, Maria A.,Pavey, John B. J.,Pinel, Catherine,Robinson, Lesley A.,Schnaubelt, Juergen,Scott, James S.,Spilling, Christopher D.,Watanabe, Hidenori,Wesson, Kieron E.,Willis, Michael C.
experimental part, p. 2874 - 2914 (2009/12/25)
For over 30 years, rapamycin has generated a sustained and intense interest from the scientific community as a result of its exceptional pharmacological properties and challenging structural features. In addition to its well known therapeutic value as a potent immunosuppressive agent, rapamycin and its derivatives have recently gained prominence for the treatment of a wide variety of other human malignancies. Herein we disclose full details of our extensive investigation into the synthesis of rapamycin that culminated in a new and convergent preparation featuring a macro-etherification/catechol-templating strategy for construction of the macrocyclic core of this natural product.
Towards the Synthesis of the C37-C42 Fragment of Rapamycin: Intramolecular Reactions of Allyl Silanes with Oxonium Ions Generated from α-Alkoxy Sulfones.
Ley, Steven V.,Kouklovsky, Cyrille
, p. 835 - 848 (2007/10/02)
A new method for the formation of methylene cyclohexane derivatives has been developed, using intramolecular trapping by allyl silanes of oxonium ions generated from α-alkoxysulfones.These acyclic precursors were prepared by quenching the anion of methoxy
