Chiral Thiazoline and Thiazole Building Blocks for the Synthesis of Peptide-Derived Natural Products

被引:20
作者
Just-Baringo, Xavier [1 ,2 ]
Albericio, Fernando [1 ,2 ,3 ,4 ]
Alvarez, Mercedes [1 ,2 ,5 ]
机构
[1] Univ Barcelona, Inst Biomed Res, E-08028 Barcelona, Spain
[2] CIBER BBN, Networking Ctr Bioengn Biomat & Nanomed, Barcelona 08028, Spain
[3] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain
[4] Univ KwaZulu Natal, Sch Chem, ZA-4001 Durban, South Africa
[5] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
关键词
Antibiotics; chiral building blocks; peptides; thiazoles; thiazolines; thiopeptides; BACTERIAL PROTEIN-SYNTHESIS; FRAGMENT A-C; CONVENIENT SYNTHESIS; CYCLIC PEPTIDE; STEREOCHEMICAL ASSIGNMENT; DEHYDRATIVE CYCLIZATION; THIOPEPTIDE ANTIBIOTICS; CYTOTOXIC METABOLITE; ASYMMETRIC-SYNTHESIS; SECONDARY ALCOHOLS;
D O I
10.2174/1568026614666140423105730
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Thiazoline and thiazole heterocycles are privileged motifs found in numerous peptide-derived natural products of biological interest. During the last decades, the synthesis of optically pure building blocks has been addressed by numerous groups, which have developed a plethora of strategies to that end. Efficient and reliable methodologies that are compatible with the intricate and capricious architectures of natural products are a must to further develop their science. Structure confirmation, structure-activity relationship studies and industrial production are fields of paramount importance that require these robust methodologies in order to successfully bring natural products into the clinic. Today's chemist toolbox is assorted with many powerful methods for chiral thiazoline and thiazole synthesis. Ranging from biomimetic approaches to stereoselective alkylations, one is likely to find a suitable method for their needs.
引用
收藏
页码:1244 / 1256
页数:13
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