Asymmetric synthesis of flavanols via Cu-catalyzed kinetic resolution of chromenes and their anti-inflammatory activity.
Journal
Science advances
ISSN: 2375-2548
Titre abrégé: Sci Adv
Pays: United States
ID NLM: 101653440
Informations de publication
Date de publication:
03 06 2022
03 06 2022
Historique:
entrez:
3
6
2022
pubmed:
4
6
2022
medline:
9
6
2022
Statut:
ppublish
Résumé
Flavanols are privileged heterocyclic compounds in medicinal chemistry. It is notable to develop an efficient and straightforward protocol for accessing chiral flavanols with precise control of the stereocenters. Here, a highly efficient kinetic resolution of chromenes was reported via Cu-catalyzed asymmetric hydroboration. This previously unidentified approach features a one-step synthesis of chiral flavan-3-ols containing two vicinal stereogenic centers via a highly efficient kinetic resolution (
Identifiants
pubmed: 35658029
doi: 10.1126/sciadv.abm9603
pmc: PMC9166297
doi:
Substances chimiques
Anti-Inflammatory Agents
0
Benzopyrans
0
Copper
789U1901C5
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
eabm9603Références
Bioorg Med Chem. 2009 Oct 15;17(20):7156-73
pubmed: 19783443
Cancer Res. 1992 Jul 15;52(14):3875-9
pubmed: 1617663
Nature. 1997 Jun 5;387(6633):561
pubmed: 9177339
J Am Chem Soc. 2017 Oct 4;139(39):13660-13663
pubmed: 28899086
J Org Chem. 2018 Nov 16;83(22):14110-14119
pubmed: 30351146
Chem Asian J. 2015 Mar;10(3):540-3
pubmed: 25585883
Int J Biol Macromol. 2017 Nov;104(Pt A):1039-1045
pubmed: 28687392
J Nat Prod. 2003 Feb;66(2):161-8
pubmed: 12608845
J Am Chem Soc. 2018 Aug 29;140(34):10687-10690
pubmed: 30114355
J Am Chem Soc. 2017 May 3;139(17):6066-6069
pubmed: 28414243
Angew Chem Int Ed Engl. 2013 Oct 25;52(44):11651-5
pubmed: 24027174
J Org Chem. 2008 Jun 20;73(12):4625-9
pubmed: 18498193
Chem Commun (Camb). 2010 Apr 21;46(15):2653-5
pubmed: 20449331
Angew Chem Int Ed Engl. 2013 Apr 2;52(14):3989-92
pubmed: 23440890
Chem Commun (Camb). 2011 Jan 7;47(1):298-300
pubmed: 20697639
Nat Chem. 2020 Sep;12(9):838-844
pubmed: 32601409
J Am Chem Soc. 2009 Mar 11;131(9):3160-1
pubmed: 19256564
J Am Chem Soc. 2016 Apr 6;138(13):4338-41
pubmed: 26967578
J Am Chem Soc. 2015 Jun 3;137(21):6746-9
pubmed: 25938599
Org Lett. 2016 Oct 7;18(19):4986-4989
pubmed: 27667117
Angew Chem Int Ed Engl. 2016 Jun 6;55(24):6969-72
pubmed: 27159674
J Am Chem Soc. 2009 Apr 15;131(14):5024-5
pubmed: 19301820
J Am Chem Soc. 2014 Nov 12;136(45):15833-6
pubmed: 25340304
Chem Sci. 2017 Jun 1;8(6):4558-4564
pubmed: 28936333
Nat Prod Rep. 2002 Oct;19(5):517-41
pubmed: 12430722
Angew Chem Int Ed Engl. 2018 Jan 26;57(5):1376-1380
pubmed: 29230927
J Am Chem Soc. 2014 Nov 5;136(44):15501-4
pubmed: 25325782
Angew Chem Int Ed Engl. 2001 Jan 19;40(2):284-310
pubmed: 11180317
Chem Asian J. 2017 Dec 14;12(24):3119-3122
pubmed: 29152880
Angew Chem Int Ed Engl. 2005 Jun 27;44(26):3974-4001
pubmed: 15942973
Angew Chem Int Ed Engl. 2019 Apr 8;58(16):5343-5347
pubmed: 30786133
Angew Chem Int Ed Engl. 2011 Apr 18;50(17):3950-3
pubmed: 21433238
Mol Immunol. 2017 Mar;83:46-51
pubmed: 28095349
J Agric Food Chem. 2017 Oct 11;65(40):8875-8883
pubmed: 28936872
Acta Crystallogr C Struct Chem. 2015 Jan;71(Pt 1):3-8
pubmed: 25567568
J Am Chem Soc. 2010 Feb 3;132(4):1226-7
pubmed: 20063883
Org Biomol Chem. 2014 Dec 14;12(46):9333-6
pubmed: 25327448
Org Lett. 2000 Dec 14;2(25):4063-5
pubmed: 11112644
Nat Prod Rep. 2001 Jun;18(3):310-33
pubmed: 11476484
Chem Commun (Camb). 2017 Jun 22;53(51):6844-6847
pubmed: 28603797
Org Lett. 2001 Mar 22;3(6):843-6
pubmed: 11263896
Nat Prod Res. 2019 Oct;33(20):2995-3010
pubmed: 30521402
Org Lett. 2020 Feb 7;22(3):1155-1159
pubmed: 31961693
Bioorg Med Chem Lett. 2011 Dec 1;21(23):6996-7000
pubmed: 22030031
J Nat Prod. 2000 Jul;63(7):1035-42
pubmed: 10924197
J Am Chem Soc. 2016 Jun 1;138(21):6703-6
pubmed: 27167490
Chem Sci. 2014 Jun;5(6):2277-2281
pubmed: 25705366
Nat Prod Rep. 2000 Apr;17(2):193-212
pubmed: 10821113