The stereoselective construction of all-carbon quaternary stereocenters by allylations and its application to synthetic studies of natural products

被引：0
作者：
Sakama A. [1 ]
Ogura A. [1 ]
Yoshida K. [2 ]
Takao K. [1 ]
机构：
[1] Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama
[2] Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya
来源：
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry | 2020年 / 78卷 / 11期
关键词：
Allylation;
D O I：
10.5059/yukigoseikyokaishi.78.1039
中图分类号：
学科分类号：
摘要：
The synthesis of organic compounds containing all.. carbon quaternary stereocenters through the addition of allylmetals to aldehydes is still a challenge. In this account we describe two methods to achieve this transformation stereoselectively: One involves the zinc-mediated Barbier-type allylation and the other allylboration of a sugar.. derived aldehyde. These methods were applied to the total synthesis of (+)-vibsanin A, and the synthesis of the tricyclic core of (-)-callophycoic acid A. © 2020 Society of Synthetic Organic Chemistry. All rights reserved.
引用
收藏
页码：1039 / 1047
页数：8
相关论文
共 52 条
[1]  
Corey E. J., Guzman, Perez A., Angew. Chem. Int. Ed, 37, (1998)
[2]  
Christoffers J., Mann A., Angew. Chem. Int. Ed, 40, (2001)
[3]  
Denissova I., Barriault L., Tetrahedron, 59, (2003)
[4]  
Christoffers J., Baro A., Adv. Synth. Catal, 347, (2005)
[5]  
Trost B. M., Jiang C., Synthesis, (2006)
[6]  
Cozzi P. G., Hilgraf R., Zimmermann N., Eur. J. Org. Chem, (2007)
[7]  
Bella M., Gasperi T., Synthesis, (2009)
[8]  
Hawner C., Alexakis A., Chem. Commun, 46, (2010)
[9]  
Das J. P., Marek I., Chem. Commun, 47, (2011)
[10]  
Hong A. Y., Stolz B. M., Eur. J. Org. Chem, (2013)
123456