A Comprehensive History of Arynes in Natural Product Total Synthesis

被引:761
|
作者
Tadross, Pamela M. [1 ]
Stoltz, Brian M. [1 ]
机构
[1] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA
关键词
STEREOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; CONCISE TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; INTRAMOLECULAR CYCLO-ADDITION; CATALYZED 2+2+2 COCYCLIZATION; BENZYNE-FURAN CYCLOADDITIONS; POTENT ANTITUMOR ANTIBIOTICS; DIRECT ACYL-ALKYLATION; DIELS-ALDER REACTIONS;
D O I
10.1021/cr200478h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A comprehensive historical review of arynes in natural product total synthesis is presented. Researchers accomplished the task of generating total syntheses, which utilized arynes in ways that built complexity or introduced motifs essential to the completion of their targets. The methods by which the researchers accomplished this task reflected the versatility of arynes as reactive intermediates for synthesis. The first instance in which arynes were applied to the total synthesis of natural products was reported by Kametani and coworkers at Tohoku University in 1967. Kametani's synthesis of cryptaustoline and cryptowoline marked the beginning of a long-term research program to utilize aryne intermediates in alkaloid synthesis that would continue for a period of more than 10 years.
引用
收藏
页码:3550 / 3577
页数:28
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