Selective palladium-catalyzed functionalization of ?-methylene butanolides

被引:0
作者
Talbi, Arbia [1 ,2 ]
Arfaoui, Aicha [2 ]
Efrit, Mohamed Lotfi [2 ]
Gaucher, Anne [1 ]
M'Rabet, Hedi [2 ]
Prim, Damien [1 ]
机构
[1] Univ Paris Saclay, CNRS, Inst Lavoisier Versailles, UVSQ, F-78035 Versailles, France
[2] Univ Tunis El Manar, Fac Sci Tunis, Lab Synth Organ & Heterocycl Select Evaluat Act Bi, Campus Univ, Tunis 2092, Tunisia
关键词
Butyrolactone; Butenolide; Palladium; STEREOSELECTIVE-SYNTHESIS; GAMMA-BUTYROLACTONES; SUBSTITUTED ALPHA; TUMOR INHIBITORS; CROSS-METATHESIS; HECK REACTION; LACTONES; NORDITERPENOIDS; CYTOTOXICITY; CONSTITUENTS;
D O I
10.1016/j.tet.2022.132926
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe an efficient and selective functionalization of a-methylene-y-butyrolactone. The two-step sequence involves the preparation of bromomethylene butyrolactone 2 in good yield prior to a palladium-catalyzed coupling process. The latter allowed the installation of aryl, alkenyl, and alkynyl groups under Suzuki-Miyaura, Heck, and Sonogashira cross-coupling conditions. The reaction sequences involving Pd(dppf)Cl-2-CsF, Pd(OAc)(2)-PPh3-Ag2CO3, Pd(PPh4)(4)-CuI-Et3N as the corresponding catalytic systems allow the preparation of an unprecedented panel of a-unsaturated substituted butyrolactones 4 -16 ranging from moderate to excellent yields. In all cases, the E-configuration of the exo-double bond is retained from the starting materials to the targets, regardless of the nature of the substituent introduced. (C) 2022 Elsevier Ltd. All rights reserved.
引用
收藏
页数:5
相关论文
共 31 条
[1]   Palladium(II)-catalyzed enyne cyclization strategies toward the podophyllotoxin ring system [J].
Abrams, Jason N. ;
Zhao, Qi ;
Ghiviriga, Ion ;
Minaruzzaman .
TETRAHEDRON, 2012, 68 (02) :423-428
[2]   Scabrolides E-G, three new norditerpenoids from the soft coral Sinularia scabra [J].
Ahmed, AF ;
Su, JH ;
Kuo, YH ;
Sheu, JH .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (12) :2079-2082
[3]  
Arcadi A, 2001, EUR J ORG CHEM, V2001, P3165
[4]   Palladium-catalyzed arylation of α-methylene-γ-butyrolactone:: 3-benzylfuran-2(5H)-ones vs (Z)-benzylidene-γ-butyrolactones and their reduction to 3-benzyl-γ butyrolactones [J].
Arcadi, A ;
Chiarini, M ;
Marinelli, F ;
Berente, Z ;
Kollàr, L .
ORGANIC LETTERS, 2000, 2 (01) :69-72
[5]   Synthetic Transformations of Methylenelactones of Eudesmanic Type. Behavior of Isoalantolactone under the Conitions of Heck Reaction [J].
Belovodskii, A. V. ;
Shults, E. E. ;
Shakirov, M. M. ;
Bagryanskaya, I. Yu. ;
Gatilov, Yu. V. ;
Tolstikov, G. A. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (11) :1719-1734
[6]   A long chain alkylated α-methylene-γ-butyrolactone from Artabotrys odoratissimus fruit [J].
Bordoloi, Prasanta K. ;
Bhuyan, Purnajyoti D. ;
Boruah, Paran ;
Bordoloi, Manobjyoti ;
Rao, Paruchuri G. .
PHYTOCHEMISTRY LETTERS, 2009, 2 (01) :22-24
[7]   Application of a new combination of palladium and CaCO3 for an aerobic heck reaction using arenediazonium-salts [J].
Brunner, H ;
de Courcy, NLC ;
Genêt, JP .
TETRAHEDRON LETTERS, 1999, 40 (26) :4815-4818
[8]   Stereoselective synthesis of α-alkylidene- and substituted alkylidene-γ-lactones [J].
Castulík, J ;
Mazal, C .
TETRAHEDRON LETTERS, 2000, 41 (15) :2741-2744
[9]   Cytotoxicity of extractives from Taiwania cryptomerioides heart-wood [J].
Chang, ST ;
Wang, DSY ;
Wu, CL ;
Shiah, SG ;
Kuo, YH ;
Chang, CJ .
PHYTOCHEMISTRY, 2000, 55 (03) :227-232
[10]   Antitubercular constituents from the stem wood of Cinnamomum kotoense [J].
Chen, FC ;
Peng, CF ;
Tsai, IL ;
Chen, IS .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (09) :1318-1323