Total synthesis of rapamycin.

Journal article

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.

Authors: Ley, S; Tackett, M; Maddess, M; Anderson, J; Brennan, P

• Publication status: Published
• Journal: Chemistry (Weinheim an der Bergstrasse, Germany)
• Volume: 15
• Issue: 12
• Pages: 2874-2914
• Publication date: 2009-01-01
• DOI: 10.1002/chem.200801656
• EISSN: 1521-3765
• ISSN: 0947-6539
• Language: English
• Keywords: Immunosuppressive Agents; Cyclization; Molecular Structure; Humans; Sirolimus; Antineoplastic Agents; Biological Agents