A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues

被引:57
作者
Bertrand, Myra Beaudoin [1 ]
Wolfe, John P. [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
D O I
10.1021/ol0606435
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new stereoselective synthesis of the antifungal and antitumor agents Preussin and 3-epi-Preussin via a Pd-catalyzed carboamination of a protected amino alcohol is described. The key transformation leads to simultaneous formation of the N-C2 bond and the C1'-aryl bond, and allows installation of the aryl group one step from the end of the sequence. This strategy permits the facile construction of a variety of preussin analogues bearing different aromatic groups.
引用
收藏
页码:2353 / 2356
页数:4
相关论文
共 34 条
[1]   Inhibition of cyclin-dependent kinase activity and induction of apoptosis by preussin in human tumor cells [J].
Achenbach, TV ;
Slater, EP ;
Brummerhop, H ;
Bach, T ;
Müller, R .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2000, 44 (10) :2794-2801
[2]  
Bach T, 2000, CHEM-EUR J, V6, P3838, DOI 10.1002/1521-3765(20001016)6:20<3838::AID-CHEM3838>3.0.CO
[3]  
2-1
[4]  
Bach T, 1998, ANGEW CHEM INT EDIT, V37, P3400, DOI 10.1002/(SICI)1521-3773(19981231)37:24<3400::AID-ANIE3400>3.0.CO
[5]  
2-3
[6]   Total syntheses of Kelsoene and Preussin [J].
Basler, B ;
Brandes, S ;
Spiegel, A ;
Bach, T .
NATURAL PRODUCTS SYNTHESIS I: TARGETS METHODS CONCEPTS, 2005, 243 :1-42
[7]   Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides [J].
Bertrand, MB ;
Wolfe, JP .
TETRAHEDRON, 2005, 61 (26) :6447-6459
[8]   Total synthesis of (+)-preussin: Control of the stereogenic centers by enantioselective allyltitanations [J].
Canova, S ;
Bellosta, V ;
Cossy, J .
SYNLETT, 2004, (10) :1811-1813
[9]   Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines [J].
Cogan, DA ;
Liu, GC ;
Ellman, J .
TETRAHEDRON, 1999, 55 (29) :8883-8904
[10]   Asymmetric synthesis of (+)-preussin from N-sulfinyl δ-amino β-ketoesters [J].
Davis, FA ;
Deng, JH .
TETRAHEDRON, 2004, 60 (23) :5111-5115