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Total Synthesis of Halipeptins A and D and Analogues
Author(s) -
Nicolaou K. C.,
Kim David W.,
Schlawe Daniel,
Lizos Dimitrios E.,
de Noronha Rita G.,
Longbottom Deborah A.
Publication year - 2005
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.200500702
Subject(s) - thiazoline , chemistry , peptide , sulfur , stereochemistry , ring (chemistry) , biochemistry , organic chemistry
Deceptive rings : Halipeptins A ( 1 a ) and D ( 1 b ) and analogues thereof were synthesized from fragments 2 and 3 a, b , respectively. Key steps included peptide‐bond formation, DAST‐induced thiazoline construction, and macrolactamization. Unlike the naturally isolated (and possibly contaminated) material, synthetic 1 b exhibited only weak toxicity against tumor cells. DAST=(diethylamino)sulfur trifluoride.