Catalytic Enantioselective Total Synthesis of (-)-Pyridovericin

被引:4
作者
Schmid, Fabian [1 ]
Bernasconi, Maurizio [1 ]
Jessen, Henning J. [1 ]
Pfaltz, Andreas [1 ]
Gademann, Karl [1 ]
机构
[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland
来源
SYNTHESIS-STUTTGART | 2014年 / 46卷 / 07期
基金
瑞士国家科学基金会;
关键词
pyridovericin; total synthesis; natural products; hydrogenation; asymmetric catalysis; PYRIDONE ALKALOIDS; PYRIDOVERICIN; ACIDS;
D O I
10.1055/s-0033-1340868
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first enantioselective catalytic total synthesis of (-)-pyridovericin is reported. The key steps involve a modified HWE reaction under aqueous conditions and an asymmetric iridium-catalyzed hydrogenation. This resulted in a highly modular and stereoselective approach that delivered the target natural product in high yield and stereoselectivity.
引用
收藏
页码:864 / 870
页数:7
相关论文
共 28 条
[1]   Total synthesis of pyridovericin: Studies toward the biomimetic synthesis of pyridomacrolidin [J].
Baldwin, JE ;
Adlington, RM ;
Conte, A ;
Irlapati, NR ;
Marquez, R ;
Pritchard, GJ .
ORGANIC LETTERS, 2002, 4 (13) :2125-2127
[2]   HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[3]  
De Sanctis M., 2013, INT C ADV TECHN ENG, P1
[4]   Directed Orthometalation and the Asymmetric Total Synthesis of N-Deoxymilitarinone A and Torrubiellone B [J].
Ding, Feiqing ;
William, Ronny ;
Leow, Min Li ;
Chai, Hua ;
Fong, Jacqueline Zi Mei ;
Liu, Xue-Wei .
ORGANIC LETTERS, 2014, 16 (01) :26-29
[5]   NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist [J].
Fulmer, Gregory R. ;
Miller, Alexander J. M. ;
Sherden, Nathaniel H. ;
Gottlieb, Hugo E. ;
Nudelman, Abraham ;
Stoltz, Brian M. ;
Bercaw, John E. ;
Goldberg, Karen I. .
ORGANOMETALLICS, 2010, 29 (09) :2176-2179
[6]  
Ganic A., 2013, THESIS U BASEL SWITZ
[7]   PHOSPHORORGANISCHE VERBINDUNGEN .12. PHOSPHINOXYDE ALS OLEFINIERUNGSREAGENZIEN [J].
HORNER, L ;
HOFFMANN, H ;
WIPPEL, HG .
CHEMISCHE BERICHTE-RECUEIL, 1958, 91 (01) :61-63
[8]   Synthesis of six-membered compounds by environmentally friendly cyclization using indirect electrolysis [J].
Ihara, M ;
Katsumata, A ;
Setsu, F ;
Tokunaga, Y ;
Fukumoto, K .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :677-684
[9]   Pyridone and Tetramic Acid Alkaloids from the Spider Pathogenic Fungus Torrubiella sp BCC 2165 [J].
Isaka, Masahiko ;
Chinthanom, Panida ;
Supothina, Sumalee ;
Tobwor, Punsa ;
Hywel-Jones, Nigel L. .
JOURNAL OF NATURAL PRODUCTS, 2010, 73 (12) :2057-2060
[10]   Chiral building-blocks by chemoenzymatic desymmetrization of 2-ethyl-1,3-propanediol for the preparation of biologically active natural products [J].
Izquierdo, I ;
Plaza, MT ;
Rodríguez, M ;
Tamayo, J .
TETRAHEDRON-ASYMMETRY, 1999, 10 (03) :449-455