143236-59-3Relevant 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.
scheme or table, 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.
Synthetic Investigations of Rapamycin. 1. Synthesis of a C10-C21 Fragment
Meyer, Stephanie D.,Miwa, Tetsuo,Nakatsuka, Masashi,Schreiber, Stuart L.
, p. 5058 - 5060 (2007/10/02)
Phosphine oxide 2, representing the C10-C21 portion of rapamycin, was stereoselectively synthesized and was demonstrated to undergo a Horner-Wittig reaction to form triene 25 as an 8:1 mixture of trans-cis isomers.
