146404-46-8Relevant academic research and scientific papers
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.
supporting information; 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.
Efficient removal of pipecolinate from rapamycin and FK506 by reaction with n-Bu4N+CN-
Luengo, Juan I.,Rozamus, Leonard W.,Holt, Dennis A.
, p. 4599 - 4602 (2007/10/02)
The reaction of rapamycin (1) and FK506 (11) with n-Bu4N+CN- / aq. THF results in an efficient excision of their pipecolinate subunits, leading in good yields to compounds 3 and 12, respectively. Two sequential ring cleava
DEGRADATION OF RAPAMYCIN: RETRIEVAL OF MAJOR INTACT SUBUNITS.
Yohannes, Daniel,Danishefsky, Samuel J.
, p. 7469 - 7472 (2007/10/02)
The degradation of rapamycin has made available key substructures which have defined the structures of advanced synthetic intermediates.
