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Total Synthesis of the Nematicidal Cyclododecapeptide Omphalotin A by Using Racemization‐Free Triphosgene‐Mediated Couplings in the Solid Phase
Author(s) -
Thern Bernd,
Rudolph Joachim,
Jung Günther
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020703)41:13<2307::aid-anie2307>3.0.co;2-y
Subject(s) - triphosgene , racemization , solid phase synthesis , phase (matter) , chemistry , amino acid , peptide synthesis , organic chemistry , combinatorial chemistry , biochemistry , peptide , phosgene
Racemization‐free coupling of Fmoc‐ N ‐methyl amino acids on a solid support is quantitative with a new triphosgene‐activation method. With this method, the total synthesis of the nematicidal cyclododecapeptide omphalotin A (see picture) was accomplished, which because of its high content of N ‐methyl amino acids had not yet been accessible.