The Catalytic Enantioselective Total Synthesis of (+)-Liphagal

被引:69
作者
Day, Joshua J. [1 ,2 ]
McFadden, Ryan M. [1 ,2 ]
Virgil, Scott C. [1 ,2 ]
Kolding, Helene [1 ,2 ]
Alleva, Jennifer L. [1 ,2 ]
Stoltz, Brian M. [1 ,2 ]
机构
[1] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA
[2] CALTECH, Div Chem & Chem Engn, Caltech Ctr Catalysis & Chem Synth, Pasadena, CA 91125 USA
关键词
arynes; asymmetric catalysis; natural products; terpenoids; total synthesis; ASYMMETRIC ALLYLIC ALKYLATION; PHOSPHOINOSITIDE 3-KINASE INHIBITORS; ALLYLATION REACTION; ENOL CARBONATES; QUATERNARY STEREOCENTERS; ALPHA-FLUOROKETONES; TSUJI ALLYLATION; ACYCLIC KETONES; LIPHAGAL; DECARBOXYLATION;
D O I
10.1002/anie.201101842
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ring a ding: The meroterpenoid natural product (+)-liphagal has been synthesized enantioselectively in 19 steps from commercially available materials. The trans-homodecalin system was achieved by ring expansion followed by stereoselective hydrogenation. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:6814 / 6818
页数:5
相关论文
共 73 条
[1]   Enantioselective Total Synthesis of the Selective PI3 Kinase Inhibitor Liphagal [J].
Alvarez-Manzaneda, Enrique ;
Chahboun, Rachid ;
Alvarez, Esteban ;
Cano, M. Jose ;
Haidour, Ali ;
Alvarez-Manzaneda, Ramon .
ORGANIC LETTERS, 2010, 12 (20) :4450-4453
[2]   The enantioselective Tsuji allylation [J].
Behenna, DC ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045
[3]   Unexpected effect of the fluorine atom on the optimal ligand-to-palladium ratio in the enantioselective Pd-catalyzed allylation reaction of fluorinated enol carbonates [J].
Belanger, Etienne ;
Houze, Clement ;
Guimond, Nicolas ;
Cantin, Katy ;
Paquin, Jean-Francois .
CHEMICAL COMMUNICATIONS, 2008, (28) :3251-3253
[4]   Enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers [J].
Belanger, Etienne ;
Cantin, Katy ;
Messe, Olivier ;
Tremblay, Melanie ;
Paquin, Jean-Francois .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1034-1035
[5]   Use of 5,5-(Dimethyl)-i-Pr-PHOX as a Practical Equivalent to t-Bu-PHOX in Asymmetric Catalysis [J].
Belanger, Etienne ;
Pouliot, Marie-France ;
Paquin, Jean-Francois .
ORGANIC LETTERS, 2009, 11 (10) :2201-2204
[6]   A new approach to dihydrobenzofurans and dihydrobenzopyrans (chromans) based on the intramolecular trapping by alcohols of benzynes generated from 7-substituted-1-aminobenzotriazoles [J].
Birkett, MA ;
Knight, DW ;
Little, PB ;
Mitchell, MB .
TETRAHEDRON, 2000, 56 (07) :1013-1023
[7]   New developments in stereoselective palladium-catalyzed allylic alkylations of preformed enolates [J].
Braun, M ;
Meier, T .
SYNLETT, 2006, (05) :661-676
[8]  
Braun M, 2000, ANGEW CHEM INT EDIT, V39, P3494, DOI 10.1002/1521-3773(20001002)39:19<3494::AID-ANIE3494>3.0.CO
[9]  
2-4
[10]  
Braun M., 2000, ANGEW CHEM, V112, P3637