Stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its C-4 epimer

作者: Jorge García-Fortanet , Miguel Carda , J. Alberto Marco

DOI: 10.1016/J.TET.2007.09.080

关键词:

摘要: Abstract A convergent stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its non-natural epimer at C-4 is described. key aspect was construction a trans-2,3-disubstituted cyclohexanone system by means Michael addition/α-alkylation sequence. The macrolactone ring either stereoisomer created using Mitsunobu Yamaguchi procedures, respectively.

参考文章(50)
P Shrimankar, L Stordal, R Maurer, Purification and characterization of a mutant DnaB protein specifically defective in ATP hydrolysis. Journal of Bacteriology. ,vol. 174, pp. 7689- 7696 ,(1992) , 10.1128/JB.174.23.7689-7696.1992
M Grompe, J Versalovic, T Koeuth, J R Lupski, Mutations in the Escherichia coli dnaG gene suggest coupling between DNA replication and chromosome partitioning. Journal of Bacteriology. ,vol. 173, pp. 1268- 1278 ,(1991) , 10.1128/JB.173.3.1268-1278.1991
René Csuk, Martina Schaade, Fluoride mediated reactions of lactones with silyl ketene acetals Tetrahedron. ,vol. 50, pp. 3333- 3348 ,(1994) , 10.1016/S0040-4020(01)87014-9
Junji Tanaka, Shuji Kanemasa, Yusuke Ninomiya, Otohiko Tsuge, A Michael Addition and Alkylation Sequence Using Methyl 2-(Trimethylsilyl)propenoate. Stereoselective Synthesis of α-Silyl Esters Bulletin of the Chemical Society of Japan. ,vol. 63, pp. 476- 483 ,(1990) , 10.1246/BCSJ.63.476
Joëlle Prunet, Recent Methods for the Synthesis of (E)-Alkene Units in Macrocyclic Natural Products Angewandte Chemie International Edition. ,vol. 42, pp. 2826- 2830 ,(2003) , 10.1002/ANIE.200301628
A. Parenty, X. Moreau, J.-M. Campagne, Macrolactonizations in the Total Synthesis of Natural Products Chemical Reviews. ,vol. 106, pp. 911- 939 ,(2006) , 10.1021/CR0301402
Samuel J. Danishefsky, Bruno Simoneau, Total syntheses of ML-236A and compactin by combining the lactonic (silyl) enolate rearrangement and aldehyde-diene cyclocondensation technologies Journal of the American Chemical Society. ,vol. 111, pp. 2599- 2604 ,(1989) , 10.1021/JA00189A038