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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.

Original publication

DOI

10.1002/chem.200801656

Type

Journal article

Journal

Chemistry

Publication Date

2009

Volume

15

Pages

2874 - 2914

Keywords

Antineoplastic Agents, Biological Products, Cyclization, Humans, Immunosuppressive Agents, Molecular Structure, Sirolimus