Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts.

[*] C. A. Lewis, Prof. S. J. Miller Department of Chemistry Boston College Chestnut Hill, MA 02467 (USA) E-mail: scott.miller@yale.edu [] Current address Department of Chemistry Yale University P.O. Box 208107 New Haven, CT 06520 (USA) Fax: (+1) 203-432-6144 [**] We thank the National Institute of General Medical Sciences for support (R01-GM-068649). Supporting information for this article is available on the WWW under http://www.angewandte.org or from the author. Communications

[1]  Scott J. Miller,et al.  Structure-selectivity relationships and structure for a peptide-based enantioselective acylation catalyst. , 2004, Journal of the American Chemical Society.

[2]  Claudio Toniolo,et al.  Control of peptide conformation by the Thorpe-Ingold effect (C?-tetrasubstitution) , 2001 .

[3]  J. Everett,et al.  Ketone–hemiacetal tautomerism in erythromycin A in non-aqueous solutions. An NMR spectroscopic study , 1991 .

[4]  T. Perun,et al.  Chemical modifications of erythromycin antibiotics. 3. Synthesis of 4" and 11 esters of erythromycin A and B. , 1972, Journal of medicinal chemistry.

[5]  A Ganesan,et al.  Natural products and combinatorial chemistry: back to the future. , 2004, Current opinion in chemical biology.

[6]  Scott J. Miller,et al.  Selection of enantioselective acyl transfer catalysts from a pooled peptide library through a fluorescence-based activity assay: an approach to kinetic resolution of secondary alcohols of broad structural scope. , 2001, Journal of the American Chemical Society.

[7]  J. W. Smith,et al.  [Ilotycin, a new antibiotic]. , 1952, Schweizerische medizinische Wochenschrift.

[8]  J. Petersen,et al.  Double Asymmetric Synthesis and a New Strategy for Stereochemical Control in Organic Synthesis , 1985 .

[9]  U. Abel,et al.  Modern methods to produce natural-product libraries. , 2002, Current opinion in chemical biology.

[10]  Scott J. Miller,et al.  Incorporation of Peptide Isosteres into Enantioselective Peptide-Based Catalysts as Mechanistic Probes. , 2001, Angewandte Chemie.

[11]  Stuart L Schreiber,et al.  Generating Diverse Skeletons of Small Molecules Combinatorially , 2003, Science.

[12]  Christopher T. Walsh,et al.  Lessons from natural molecules , 2004, Nature.

[13]  S. Gellman,et al.  Stereochemical Requirements for β-Hairpin Formation: Model Studies with Four-Residue Peptides and Depsipeptides , 1996 .

[14]  S. Masamune,et al.  Doppelte Stereodifferenzierung und eine neue Strategie zur Stereokontrolle in der Organischen Synthese , 1985 .

[15]  I. Karle,et al.  A designed beta-hairpin peptide in crystals. , 1996, Proceedings of the National Academy of Sciences of the United States of America.

[16]  Scott J. Miller,et al.  Catalytic enantioselective synthesis of sulfinate esters through the dynamic resolution of tert-butanesulfinyl chloride. , 2004, Journal of the American Chemical Society.