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Total Synthesis of the Thiazolyl Peptide GE2270 A
Author(s) -
Müller H. Martin,
Delgado Oscar,
Bach Thorsten
Publication year - 2007
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/anie.200700684
Subject(s) - stille reaction , intramolecular force , peptide , peptide bond , chemistry , total synthesis , yield (engineering) , stereochemistry , pyridine , combinatorial chemistry , sequence (biology) , computer science , organic chemistry , biochemistry , catalysis , materials science , metallurgy
When one door closes, another opens: In the synthesis of the thiazolyl peptide GE2270 A ( 1 ), the bonds labeled I and II at the pyridine core were established by two consecutive cross‐coupling reactions. Amide bond formation ( IV ) and subsequent intramolecular Stille reaction ( III ) were more effective than the originally conceived connection strategy ( III before IV ). GE2270 A ( 1 ) was prepared with an overall yield of 4.8 % in 20 steps along the longest linear sequence.