[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
[51]  
Trost B.M., Lee C.B., J. Am. Chem. Soc., 123, (2001)
[52]  
Saito S., Kuroda A., Matsunaga H., Ikeda S., Tetrahedron, 52, (1996)
[53]  
Frauenrath H., Houben-Weyl, Methods of Organic Chemistry, E21, (1995)
[54]  
Pereira S., Srebnik M., Aldrichimica Acta, 26, (1993)
[55]  
Chai Y., Hong S.-P., Lindsay H.A., McFarland C., McIntosh M.C., Tetrahedron, 58, (2002)
[56]  
Carlsen P.H.J., Katsuki T., Martin V.S., Sharpless K.B., J. Org. Chem., 46, (1981)
[57]  
Mathre J., Jones T.K., Xavier L.C., Blacklock T.J., Reamer R.A., Mohan J.J., Jones E.T., Hoogsteen K., Baum M.W., Grabowski E.J., J. Org. Chem., 56, (1991)
[58]  
Bach J., Berenguer R., Garcia J., Lopez M., Manzanal J., Vilarrasa J., J. Org. Chem., 61, (1996)
[59]  
Bicking J.B., Robb C.M., Smith R.L., Cragoe Jr. E.J., Kuehl Jr. F.A., Mandel L.R., J. Med. Chem., 20, (1977)
[60]  
Knothe G., Bagby M.O., Weisleder D., J. Am. Oil Chem. Soc., 72, (1995)
123456