Highlighting the Rich Chemistry of the Allenone Moiety

被引:15
作者
Alonso, Jose M. [1 ]
Almendros, Pedro [2 ]
机构
[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ, Unidad Asociada CSIC,Grp Lactamas & Heterociclos, Madrid 28040, Spain
[2] CSIC, Inst Quim Organ Gen, IQOG, Juan Cierva 3, Madrid 28006, Spain
关键词
allenes; cyclization; ketones; regioselectivity; synthetic methods; METHYLENE-GAMMA-BUTYROLACTONES; ASYMMETRIC CONJUGATE ADDITION; CATALYZED AEROBIC OXIDATION; POT CASCADE REACTIONS; EFFICIENT SYNTHESIS; 1,2-ALLENIC KETONES; C-C; CYCLIZATION REACTION; ENANTIOSELECTIVE SYNTHESIS; CHIRALITY TRANSFER;
D O I
10.1002/adsc.202300076
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Conjugated and non-conjugated allenones appear as recurring motifs in organic synthesis, natural products and mechanistic investigations showing unique properties and applications. The ability of allenones to build cycles has provided a direct access to strained systems, medium-sized rings, arenes, heterocycles and complex polycycles. In addition, allenones have served as models in mechanistic investigations and catalysis. The critic compilation herein presented will provide an exhaustive overview of the synthetic possibilities allenones may offer, which certainly will inspire our community in their search of more efficient synthetic methodologies, preparation of biological and pharmaceutical targets, and improve our knowledge in theoretical organic chemistry. Great part of this review will discuss synthetic aspects, catalysis innovation and mechanistic insights of the chemical transformations implying the allenone motif. In addition, many examples on total synthesis and pharmacologically active compounds will be described. We hope that this overview will be attractive to the organic chemistry, synthetic chemistry, catalysis, theoretical chemistry, natural products and medicinal chemistry communities.
引用
收藏
页码:1332 / 1384
页数:53
相关论文
共 295 条
[1]   MEGASTIGMANES AND FLAVONOIDS FROM THE LEAVES OF SCORODOCARPUS-BORNEENSIS [J].
ABE, F ;
YAMAUCHI, T .
PHYTOCHEMISTRY, 1993, 33 (06) :1499-1501
[2]   Divergent Halogenation Pathways of 2,2-Dichlorobut-3-yn-1-ols to 3-Chloro-4-Iodofurans and α-Chloro-γ-Iodoallenes: Electrophilic versus Pd(II)-Catalyzed Halogenation Strategies [J].
Abozeid, Mohamed Ahmed ;
Kim, Hun Young ;
Oh, Kyungsoo .
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (23) :5368-5373
[3]   Allene substitution-controlled switching of dimerization to cycloisomerization in the PdII-catalyzed reaction of terminal α-allenones [J].
Alcaide, Benito ;
Almendros, Pedro ;
Martinez del Campo, Teresa .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (17) :2844-2849
[4]   Carbonyl allenylation/free radical cyclization sequence as a new regio- and stereocontrolled access to bi- and tricyclic β-lactams [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina ;
Redondo, Maria C. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (05) :1604-1608
[5]   Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality [J].
Alonso, Jose M. ;
Almendros, Pedro .
CHEMICAL REVIEWS, 2021, 121 (07) :4193-4252
[6]   Development of an Allenyne-Alkyne [4+2] Cycloaddition and its Application to Total Synthesis of Selaginpulvilin A [J].
Anh Le ;
Gupta, Saswata ;
Xu, Man ;
Xia, Yuanzhi ;
Lee, Daesung .
CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (56)
[7]  
[Anonymous], 2007, ANGEW CHEM, V119, P5287
[8]  
[Anonymous], 2004, Angew. Chem, V116, P1216
[9]  
[Anonymous], 2013, ANGEW CHEM, V125, P6875
[10]  
[Anonymous], 2017, ANGEW CHEM, V129, P14410