Update 1 of: Macrolactonizations in the total synthesis of natural products

被引：294
作者：
Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, F-91198 Gif sur Yvette, France [1 ]
不详 [2 ]
不详 [3 ]
机构：
[1] Institut de Chimie des Substances Naturelles, F-91198 Gif sur Yvette, Avenue de la Terrasse
[2] Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles-Saint-Quentin-en-Yvelines, 78035 Versailles Cedex
[3] Institut Charles Gerhardt, UMR5253, Ecole Nationale Supérieure de Chimie, F-34296 Montpellier
来源：
Campagne, J.-M. (jean-marc.campagne@enscm.fr) | 1600年 / American Chemical Society卷 / 113期
关键词：
858;
D O I：
10.1021/cr300129n
中图分类号：
学科分类号：
摘要：
An overview of the macrolactonization of seco-acids in the total synthesis of natural products was studied. The macrolactonization of thioesters is the biosynthetic pathway for the formation of macrolides. The most famous reaction involving a thioester is the 'double activation' method described in 1974 by Corey and Nicolaou. The mechanism involves the initial formation of a 2-pyridine thioester of the ω-hydroxy acid via a Mukaiyama oxidation, reduction condensation with PySSPy and triphenylphosphine. To avoid dimer formation, the reaction is usually carried out in a one-pot, two-step process. The use of cyanuric chloride in macrolactonizations was introduced by Venkataraman in 1980. The mechanism of this reaction, closely related to the mechanism invoked in the Corey-Nicolaou macrolactonizations, involves a double-activation mechanism. Shiina and Mukaiyama have developed an alternative strategy based on the Rh-catalyzed formation of a cyclic silyl siloxycarboxylate intermediate, which is, in turn, treated with Me2Si(OTf)2 to give the corresponding lactones in high yields.
引用
收藏
页码：PR1 / PR40
页数：39
相关论文
共 420 条
[1]  
Kerschbaum M., Chem. Ber., 60, (1927)
[2]  
Tapiolas D.M., Roman M., Fenical W., Stout T.J., Clardy J., J. Am. Chem. Soc., 113, (1991)
[3]  
Hayakawa Y., Shinya K., Furihata K., Seto H., J. Am. Chem. Soc., 115, (1993)
[4]  
Henninger T.C., Expert Opin. Ther. Pat., 13, (2003)
[5]  
Davies J.S., J. Peptide Sci., 9, (2003)
[6]  
Rychnovsky S.D., Chem. Rev., 95, (1995)
[7]  
Yeung K.S., Paterson I., Angew. Chem., Int. Ed. Engl., 41, (2002)
[8]  
Norcross R.D., Paterson I., Chem. Rev., 95, (1995)
[9]  
Nicolaou K.C., Ritzen A., Namoto K., J. Chem. Soc., Chem. Commun., (2001)
[10]  
Furstner A., Eur. J. Org. Chem., (2004)
12345678910