期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 3, 期 2, 页码 413-429出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200700361
关键词
antibiotics; Diels-Alder reaction; macrocyclization; natural products; total synthesis
The total syntheses of the thiopeptide antibiotics GE2270A (7), GE2270T (8), and GE2270C1 (9) are described. ne 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).
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