[3,3]-Sigmatropic Rearrangements in the Enantioselective Synthesis of (-)-Methylenolactocin

被引:0
作者
Ariza, Xavier [1 ]
Fernández, Natalia [1 ]
Garcia, Jordi [1 ]
López, Marta [1 ]
Montserrat, Laia [1 ]
Ortiz, Jordi [1 ]
机构
[1] Dept. de Quím. Orgàn., Div. III, Universitat de Barcelona, 08028, Barcelona
来源
| 1600年 / Georg Thieme Verlag卷
关键词
Asymmetric synthesis; Dihidroxylations; Diols; Rearrangement;
D O I
10.1055/s-2003-44351
中图分类号
学科分类号
摘要
A Pd(II)-catalyzed [3,3]-sigmatropic rearrangement is used to transfer chirality from an enantio-enriched alk-3-ene-1,2-diol to a C2- symmetrical alk-2-ene-1,4-diol which, in turn, can be converted into a precursor of (-)-methylenolactocin through an additional [3,3]-sigmatropic rearrangement (either Johnson orthoester or Ireland-Claisen rearrangement).
引用
收藏
页码:128 / 134
页数:6
相关论文
共 60 条
[1]  
Pichon M., Figadere B., Tetrahedron: Asymmetry, 7, (1996)
[2]  
Whitesell J.K., Chem. Rev., 89, (1989)
[3]  
Chong J.M., Clarke I.S., Koch I., Olbach P.C., Taylor N.J., Tetrahedron: Asymmetry, 6, (1995)
[4]  
Kim M.J., Lee I.S., Synlett, (1993)
[5]  
Otten S., Frohlich R., Hanfe G., Tetrahedron: Asymmetry, 9, (1998)
[6]  
Julienne K., Metzner P., Henryon V., Greiner A., J. Org. Chem., 63, (1998)
[7]  
Burk M.J., Feaster J.E., Harlow R.L., Tetrahedron: Asymmetry, 2, (1991)
[8]  
Burk M.J., Harper T.G.P., Kalberg C.S., J. Am. Chem. Soc., 117, (1995)
[9]  
Wiesaner C., Kratky C., Weissensteiner W., Tetrahedron: Asymmetry, 7, (1996)
[10]  
Amador M., Ariza X., Garcia J., Sevilla S., Org. Lett., 4, (2002)