Premium
Total Synthesis of Thiopeptide Antibiotics GE2270A, GE2270T, and GE2270C1
Author(s) -
Nicolaou K. C.,
Dethe Dattatraya H.,
Leung Gulice Y. C.,
Zou Bin,
Chen David Y.K.
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200700361
Subject(s) - pyridine , stereochemistry , chemistry , thiazole , ring (chemistry) , total synthesis , molecule , sequence (biology) , side chain , combinatorial chemistry , organic chemistry , biochemistry , polymer
The total syntheses of the thiopeptide antibiotics GE2270A ( 7 ), GE2270T ( 8 ), and GE2270C1 ( 9 ) are described. The original synthetic strategies employed utilized the hetero‐Diels–Alder reaction to construct the pyridine core of the target molecules and relied on a macrolactamization process to construct the macrocycle. The hetero‐Diels–Alder‐based strategy finally evolved allows the introduction of all four thiazole units attached to the pyridine ring and a one‐pot sequence for macrocyclization and side‐chain extension, culminating in highly convergent and expedient syntheses of these molecules as exemplified by a 24‐step synthesis of GE2270C1 ( 9 ).