Stereoselective Synthesis of Dienyl-Carboxylate Building Blocks: Formal Synthesis of Inthomycin C

被引:45
作者
Souris, Caroline [1 ]
Frebault, Frederic [1 ]
Patel, Ashay [2 ]
Audisio, Davide [1 ]
Houk, K. N. [2 ]
Maulide, Nuno [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
关键词
SMALL-MOLECULE SYNTHESIS; CYCLOBUTENE ELECTROCYCLIC REACTIONS; ASYMMETRIC ALLYLIC ALKYLATION; OXIDATION-WITTIG REACTIONS; CROSS-COUPLING REACTIONS; ORGANOBORON COMPOUNDS; VERSATILE; (+)-INTHOMYCIN-B; OXAZOLOMYCIN; COMPETITION;
D O I
10.1021/ol401226y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A direct synthesis of stereodefined halodienes is reported. Those key building blocks enable a concise access to polyenic products, as demonstrated in a modular synthesis of Inthomycin C.
引用
收藏
页码:3242 / 3245
页数:4
相关论文
共 57 条
[1]   Stereoselective synthesis of trienoic acids: Synthesis of retinoic acids and analogues [J].
Abarbri, Mohamed ;
Parrain, Jean-Luc ;
Duchene, Alain ;
Thibonnet, Jerome .
SYNTHESIS-STUTTGART, 2006, (17) :2951-2970
[2]  
[Anonymous], 2002, HDB ORGANOPALLADIUM
[3]   Diastereodivergent De-epimerization in Catalytic Asymmetric Allylic Alkylation [J].
Audisio, Davide ;
Luparia, Marco ;
Oliveira, Maria Teresa ;
Kluett, Dina ;
Maulide, Nuno .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (29) :7314-7317
[4]   A stereoselective palladium-mediated reductive coupling of electron-deficient terminal iodoalkenes [J].
Batsanov, Andrei S. ;
Knowles, Jonathan P. ;
Samsam, Benedict ;
Whiting, Andrew .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (02) :227-233
[5]  
Beletskaya I.P., 2004, COMPREHENSIVE COORDI, V9, P305
[6]   THERMAL RING CLOSURE OF SUBSTITUTED BUTA-1,3-DIENES [J].
BRUNE, HA ;
SCHWAB, W .
TETRAHEDRON, 1969, 25 (18) :4375-&
[7]   SYNTHESIS OF THE (2E,4Z,6E)-TETRAENOL, (2E,4E,6E)-TETRAENOL AND (2E,4E,6Z)-TETRAENOL STEMS OF THE HOST-SELECTIVE AK AND AF TOXINS BY HYDROMETALLATION [J].
CROMBIE, L ;
HORSHAM, MA ;
JARRETT, SRM .
TETRAHEDRON LETTERS, 1989, 30 (32) :4299-4302
[8]   SYNTHESES OF THE ETHYL-ESTERS OF THE PLANT HOST-SELECTIVE (H-S) TOXINS (AF-IIA, AF-IIC AND AK-II) PRODUCED BY PATHOTYPES OF ALTERNARIA-ALTERNATA [J].
CROMBIE, L ;
HORSHAM, MA ;
JARRETT, SRM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1511-1524
[9]   Recent Advances in Stereoselective Synthesis of 1,3-Dienes [J].
De Paolis, Michael ;
Chataigner, Isabelle ;
Maddaluno, Jacques .
STEREOSELECTIVE ALKENE SYNTHESIS, 2012, 327 :87-146
[10]   Electronic control of stereoselectivities of electrocyclic reactions of cyclobutenes: A triumph of theory in the prediction of organic reactions [J].
Dolbier, WR ;
Koroniak, H ;
Houk, KN ;
Sheu, CM .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (10) :471-477