Beilstein J. Org. Chem.2017,13, 1407–1412, doi:10.3762/bjoc.13.137
as readily available starting material.
Keywords: antibiotic; bromination; BSC; C–H arylation; cross-coupling; Hantzsch synthesis; thiopeptide; Introduction
Thiopeptide antibiotics are a class of peptide-derived macrocycles which contain many thiazole and thiazoline units, with almost 90 structures
by using two developed innovative cross-coupling reactions, the palladium-catalyzed direct C–H (hetero)arylation of thiazole-4-carboxylate [21] and a palladium-catalyzed borylation-Suzuki coupling (BSC) 2-ketothiazole unit at 4-position as alternative to thiazolyltin intermediate [22]. Herein, an
improved synthetic strategy toward the structurally-related micrococcinate ester bearing a methyl ketone function (R = Me) was reported through building and direct introduction of thiazole units using BSC and Hantzsch methodologies. The final access to a novel fully orthogonally-protected heterocyclic core
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Graphical Abstract
Figure 1:
Main synthetic strategies towards heterocyclic cores of D-series GE2270 and our present one.
Beilstein J. Org. Chem.2016,12, 391–405, doi:10.3762/bjoc.12.42
a Professor at the University of Bath, he obtained his BSC from UEA (1986), PhD from the University of Victoria (1991) and was a PDRF with Seiji Shinkai in Japan (1991–1995). He was a Royal Society Research Fellow at the University of Birmingham (1995–2000), and University of Bath (2000–2003). He
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Graphical Abstract
Scheme 1:
Reaction of trimethylsilyl cyanide with tricarbonyl (η5-cyclohexadienyl)iron(1+) salts. Reproduced ...