Abstract
The five-membered oxacyclic system of furan-2(5H)-ones, commonly named as γ- butenolides or appropriately as Δα,β-butenolides, is of high interest since many studies have proven its bioactivity. During the past few years, Δα,β-butenolides have been important synthetic targets, with several reports of new procedures for their construction. A short compendium of the main different synthetic methodologies focused on the Δα,β-butenolide ring formation, along with selected examples of compounds with relevant biological activities of these promising pharmaceutical entities is presented.
Keywords: Δα, β-butenolide, butenolactone, furan-2(5H)-one, isocrotonolactone, unsaturated γ lactone, γ-butenolide.
Graphical Abstract
[http://dx.doi.org/10.18433/J3T886] [PMID: 19203472]
[http://dx.doi.org/10.1038/sj.bjp.0701076] [PMID: 9146894]
[http://dx.doi.org/10.1016/S0960-894X(01)00831-9] [PMID: 11844709]
[http://dx.doi.org/10.1016/j.bmc.2013.06.044] [PMID: 23876338]
[http://dx.doi.org/10.1002/cmdc.201200234] [PMID: 22689528]
[http://dx.doi.org/10.1016/j.neuint.2013.02.027] [PMID: 23500605]
[http://dx.doi.org/10.1016/j.bmcl.2011.06.022] [PMID: 21757344]
[http://dx.doi.org/10.1021/np100633k] [PMID: 21126094]
[http://dx.doi.org/10.1021/np900279u] [PMID: 19813754]
[http://dx.doi.org/10.1021/np060218k] [PMID: 16989537]
[http://dx.doi.org/10.1021/np100489u] [PMID: 21142112]
[http://dx.doi.org/10.1070/RC1977v046n07ABEH002162]
[http://dx.doi.org/10.1039/co9940100287]
[http://dx.doi.org/10.1039/co9950200133]
[http://dx.doi.org/10.1039/co9960300295]
[http://dx.doi.org/10.2174/1570193053544427]
[http://dx.doi.org/10.1070/RC2009v078n04ABEH003899]
[http://dx.doi.org/10.1021/acs.chemrev.7b00151] [PMID: 28640622]
[http://dx.doi.org/10.1016/j.ejmech.2019.03.021] [PMID: 30909021]
[http://dx.doi.org/10.1021/cr60230a002]
[http://dx.doi.org/10.1021/cr60303a004]
[http://dx.doi.org/10.1002/cssc.201701469] [PMID: 28834397]
[http://dx.doi.org/10.1055/s-0028-1088132]
[http://dx.doi.org/10.1021/jo020640f] [PMID: 12530910]
[http://dx.doi.org/10.1021/ja01371a059]
[http://dx.doi.org/10.1002/jhet.3398]
[http://dx.doi.org/10.1016/j.tet.2012.10.108]
[http://dx.doi.org/10.1016/j.tet.2012.03.057]
[http://dx.doi.org/10.1002/chin.199103156]
[http://dx.doi.org/10.1021/acs.orglett.5b03026] [PMID: 26551928]
[http://dx.doi.org/10.1016/S0040-4039(98)00887-9] [PMID: 30422130]
[http://dx.doi.org/10.1021/ol102994q] [PMID: 21268603]
[http://dx.doi.org/10.1021/acs.joc.8b03293] [PMID: 30807154]
[http://dx.doi.org/10.1016/j.tetlet.2007.01.053]
[http://dx.doi.org/10.1021/ja9719945]
[http://dx.doi.org/10.1016/j.tet.2007.03.100]
[http://dx.doi.org/10.1055/s-2002-34906]
[http://dx.doi.org/10.1002/cctc.200900282]
[http://dx.doi.org/10.1021/ol0504087] [PMID: 15844911]
[http://dx.doi.org/10.1021/ol9905912] [PMID: 10822563]
[http://dx.doi.org/10.1016/S0040-4039(01)84182-4]
[http://dx.doi.org/10.1002/anie.197506341]
[http://dx.doi.org/10.1021/ol102407k] [PMID: 20979406]
[http://dx.doi.org/10.1021/ol8001333] [PMID: 18288857]
[http://dx.doi.org/10.1021/ja305209w] [PMID: 22823936]
[http://dx.doi.org/10.1021/op200019k]
[http://dx.doi.org/10.1055/s-2006-950310]
[http://dx.doi.org/10.1016/j.tetasy.2007.07.027]
[http://dx.doi.org/10.1039/B604742D] [PMID: 17028738]
[http://dx.doi.org/10.1002/jhet.633]
[http://dx.doi.org/10.1039/C6OB00835F] [PMID: 27197887]
[http://dx.doi.org/10.1016/j.jorganchem.2004.07.025]
[http://dx.doi.org/10.1016/j.tetlet.2004.03.136]
[http://dx.doi.org/10.1021/ja0165234] [PMID: 11583565]
[http://dx.doi.org/10.1021/jo0205255] [PMID: 12558397]
[http://dx.doi.org/10.1021/jo701629t] [PMID: 17983242]
[http://dx.doi.org/10.3987/COM-09-S(S)8]
[http://dx.doi.org/10.1016/j.tetlet.2004.07.129]
[http://dx.doi.org/10.1039/C9QO00779B]
[http://dx.doi.org/10.1021/ol401824v] [PMID: 23905884]
[http://dx.doi.org/10.1021/ja806685j] [PMID: 19055329]
[http://dx.doi.org/10.1021/ol052160r] [PMID: 16288518]
[http://dx.doi.org/10.1002/adsc.201000762]
[http://dx.doi.org/10.1039/C6QO00328A]
[http://dx.doi.org/10.1016/j.tet.2011.07.048]
[http://dx.doi.org/10.2174/1385272821666170111151917]
[http://dx.doi.org/10.1021/acs.orglett.9b03298] [PMID: 31622107]
[http://dx.doi.org/10.1021/acs.orglett.6b03737] [PMID: 28133962]
[http://dx.doi.org/10.1021/acs.orglett.9b02982] [PMID: 31486655]
[http://dx.doi.org/10.1002/chem.201302169] [PMID: 24026870]
[http://dx.doi.org/10.1021/acs.orglett.7b02249] [PMID: 28809499]
[http://dx.doi.org/10.1021/acs.orglett.8b03718] [PMID: 30566361]
[http://dx.doi.org/10.1021/ja205674x] [PMID: 21766859]
[http://dx.doi.org/10.1021/acs.orglett.9b00574] [PMID: 30924673]
[http://dx.doi.org/10.1021/acs.orglett.8b02554] [PMID: 30204453]
[http://dx.doi.org/10.1021/jo702085p] [PMID: 18069852]
[http://dx.doi.org/10.1016/j.tetlet.2015.05.117]
[http://dx.doi.org/10.1002/anie.201908917] [PMID: 31595605]
[http://dx.doi.org/10.1016/j.tet.2019.02.042]
[http://dx.doi.org/10.1055/s-0037-1611586]
[http://dx.doi.org/10.1039/B402826K] [PMID: 15179491]
[http://dx.doi.org/10.1002/anie.201206368] [PMID: 23225348]
[http://dx.doi.org/10.1021/acs.orglett.9b00521] [PMID: 30888193]
[http://dx.doi.org/10.1021/ol400264a] [PMID: 23514430]
[http://dx.doi.org/10.1016/j.tetasy.2004.11.085]
[http://dx.doi.org/10.1055/s-0030-1259987]
[http://dx.doi.org/10.1021/acs.jafc.8b06284] [PMID: 30811195]
[http://dx.doi.org/10.1002/jhet.617]
[http://dx.doi.org/10.1016/j.tetlet.2016.08.038]
[http://dx.doi.org/10.1002/open.201200037] [PMID: 24551514]
[http://dx.doi.org/10.1080/00397911.2019.1652914]
[http://dx.doi.org/10.1055/s-0037-1609687]
[http://dx.doi.org/10.1002/ffj.3464]
[http://dx.doi.org/10.1055/s-0037-1609560]
[http://dx.doi.org/10.1021/ol071223y] [PMID: 17608489]
[http://dx.doi.org/10.1021/jacs.6b01462] [PMID: 27064419]
[http://dx.doi.org/10.1016/S0960-894X(99)00288-7] [PMID: 10406640]
[http://dx.doi.org/10.1056/NEJMp058136] [PMID: 15972862]
[http://dx.doi.org/10.1016/j.ejmech.2018.10.054] [PMID: 30396033]
[http://dx.doi.org/10.1016/j.bmc.2006.07.047] [PMID: 16904331]
[http://dx.doi.org/10.1016/j.ejphar.2007.01.008] [PMID: 17316604]
[http://dx.doi.org/10.1016/j.bmcl.2004.01.076] [PMID: 15050636]
[http://dx.doi.org/10.1016/j.bmcl.2006.06.032] [PMID: 16806914]
[http://dx.doi.org/10.1016/j.bmc.2006.10.023] [PMID: 17067801]
[http://dx.doi.org/10.1016/j.bmc.2010.07.009] [PMID: 20692174]
[PMID: 15015595]
[http://dx.doi.org/10.1021/np050145p] [PMID: 16124766]
[http://dx.doi.org/10.1016/j.phytochem.2005.08.014] [PMID: 16213536]
[http://dx.doi.org/10.1007/s12272-010-1014-7] [PMID: 21052940]
[http://dx.doi.org/10.1021/ol060062f] [PMID: 16494492]
[http://dx.doi.org/10.1007/BF02976927] [PMID: 12433188]