Concise Stereoselective Total Synthesis of Leiocarpin C

被引:4
作者
Rao, Dasireddi Chandra [1 ]
Shekhar, Vanam [1 ]
Reddy, Dorigondla Kumar [1 ]
Chinnababu, Baggu [1 ]
Venkateswarlu, Yenamandra [1 ]
机构
[1] Indian Inst Chem Technol, Div Nat Prod Chem, Nat Prod Lab, Hyderabad 500007, Andhra Pradesh, India
关键词
Goniothalamus leiocarpus; Leiocarpin C; Lactones; Hydroxylation; K-Selectride; Total synthesis; Stereoselective synthesis; STYRYL-LACTONES; STEREOCHEMISTRY; CYTOTOXICITY;
D O I
10.1002/hlca.201200656
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and highly concise strategy has been developed for the stereoselective total synthesis of leiocarpin C starting from commercially available mandelic ester. The strategy utilizes the OsO4-catalyzed cis-hydroxylation and selective reduction with K-Selectride as key steps.
引用
收藏
页码:2179 / 2184
页数:6
相关论文
共 24 条
[1]  
Blázquez MA, 1999, PHYTOCHEM ANALYSIS, V10, P161, DOI 10.1002/(SICI)1099-1565(199907/08)10:4<161::AID-PCA453>3.0.CO
[2]  
2-2
[3]   ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].
CHA, JK ;
CHRIST, WJ ;
KISHI, Y .
TETRAHEDRON, 1984, 40 (12) :2247-2255
[4]  
ChandraRao D., 2013, TETRAHEDRON LETT, V54, P828
[5]   Styryl lactones and their derivatives: Biological activities, mechanisms of action and potential leads for drug design [J].
de Fatima, A. ;
Modolo, L. V. ;
Conegero, L. S. ;
Pilli, R. A. ;
Ferreira, C. V. ;
Kohn, L. K. ;
de Carvalho, J. E. .
CURRENT MEDICINAL CHEMISTRY, 2006, 13 (28) :3371-3384
[6]   Catalytic, asymmetric Mannich-type reactions of N-acylimino esters:: Reactivity, diastereo- and enantioselectivity, and application to synthesis of N-acylated amino acid derivatives [J].
Kobayashi, S ;
Matsubara, R ;
Nakamura, Y ;
Kitagawa, H ;
Sugiura, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2507-2515
[7]   Total Synthesis of Leiocarpin C and (+)-Goniodiol via an Olefin Cross-Metathesis Protocol [J].
Krishna, Palakodety Radha ;
Alivelu, Munagala .
HELVETICA CHIMICA ACTA, 2011, 94 (06) :1102-1107
[8]  
Mereyala Hari Babu, 2001, Current Medicinal Chemistry - Anti-Cancer Agents, V1, P293, DOI 10.2174/1568011013354606
[9]  
Mu Q, 2003, PLANTA MED, V69, P826, DOI 10.1055/s-2003-43219
[10]  
Mu Q, 1999, CHINESE CHEM LETT, V10, P135