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Total Synthesis of Rapamycin

Ley, SV; Tackett, MN; Maddess, ML; Anderson, JC; Brennan, PE; Cappi, MW; ... Willis, MC; + view all (2009) Total Synthesis of Rapamycin. CHEM-EUR J , 15 (12) 2874 - 2914. 10.1002/chem.200801656.

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Abstract

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.

Type:Article
Title:Total Synthesis of Rapamycin
DOI:10.1002/chem.200801656
Keywords:anticancer agents, immunosuppressive agents, macrocyclization, natural products, total synthesis, UNIFIED TOTAL-SYNTHESIS, 1,3-DIOL ACETONIDES, ORGANIC-SYNTHESIS, IMMUNOMODULATORS (-)-RAPAMYCIN, STEREOSELECTIVE CONSTRUCTION, ASYMMETRIC DIHYDROXYLATION, BIOLOGICAL CHARACTERISTICS, ABSOLUTE STEREOCHEMISTRY, STEREOSPECIFIC SYNTHESIS, CHEMOENZYMATIC SYNTHESIS
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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