Mukaiyama aldol reaction: an effective asymmetric approach to access chiral natural products and their derivatives/analogues.
Journal
RSC advances
ISSN: 2046-2069
Titre abrégé: RSC Adv
Pays: England
ID NLM: 101581657
Informations de publication
Date de publication:
07 Nov 2023
07 Nov 2023
Historique:
received:
26
07
2023
accepted:
21
10
2023
medline:
29
11
2023
pubmed:
29
11
2023
entrez:
29
11
2023
Statut:
epublish
Résumé
The Mukaiyama aldol reaction is generally a Lewis-acid catalyzed cross-aldol reaction between an aldehyde or ketone and silyl enol ether. It was first described by Mukaiyama in 1973, almost 5 decades ago, to achieve the enantioselective synthesis of β-hydroxy carbonyl compounds in high percentage yields. Mukaiyama aldol adducts play a pivotal role in the synthesis of various naturally occurring and medicinally important organic compounds such as polyketides, alkaloids, macrolides,
Identifiants
pubmed: 38025859
doi: 10.1039/d3ra05058k
pii: d3ra05058k
pmc: PMC10631541
doi:
Types de publication
Journal Article
Review
Langues
eng
Pagination
32975-33027Informations de copyright
This journal is © The Royal Society of Chemistry.
Déclaration de conflit d'intérêts
There are no conflicts to declare.
Références
Antibiotiki. 1971 Jun;16(6):510-3
pubmed: 5000144
Nat Prod Rep. 2004 Feb;21(1):77-93
pubmed: 15039836
Chem Sci. 2022 Jul 5;13(28):8395-8400
pubmed: 35919712
Chem Rev. 2015 May 13;115(9):2975-3011
pubmed: 25906056
Org Lett. 2021 Oct 1;23(19):7439-7444
pubmed: 34494848
Mar Drugs. 2021 Mar 31;19(4):
pubmed: 33807472
J Am Chem Soc. 2022 Oct 19;144(41):18778-18783
pubmed: 36194507
Org Lett. 2018 Apr 20;20(8):2282-2286
pubmed: 29624062
Tetrahedron Lett. 1969 Jun;(27):2239-44
pubmed: 5796583
Chem Pharm Bull (Tokyo). 1997 May;45(5):947-9
pubmed: 9178529
Tetrahedron. 1967 Oct;23(10):3893-902
pubmed: 6065624
Molecules. 2022 Oct 17;27(20):
pubmed: 36296545
Proc Natl Acad Sci U S A. 2011 Apr 12;108(15):6258-63
pubmed: 21444795
PLoS One. 2017 May 23;12(5):e0176182
pubmed: 28542610
J Nat Prod. 2020 Mar 27;83(3):770-803
pubmed: 32162523
J Biol Chem. 2004 Sep 3;279(36):37832-41
pubmed: 15231837
J Org Chem. 2020 Aug 7;85(15):10125-10135
pubmed: 32668903
Angew Chem Int Ed Engl. 2021 Jan 11;60(2):635-639
pubmed: 32969565
Nat Prod Rep. 2008 Oct;25(5):854-61
pubmed: 18820754
Chem Pharm Bull (Tokyo). 2022;70(10):740-747
pubmed: 36184458
Chem Pharm Bull (Tokyo). 2020;68(4):380-383
pubmed: 32238655
J Antibiot (Tokyo). 1980 Sep;33(9):1054-62
pubmed: 7440410
J Am Chem Soc. 2021 Jul 21;143(28):10590-10595
pubmed: 34237219
Pharmaceuticals (Basel). 2021 Sep 19;14(9):
pubmed: 34577639
Chemistry. 2023 Jan 27;29(6):e202203004
pubmed: 36305658
J Org Chem. 2021 Jun 4;86(11):7537-7551
pubmed: 34014095
J Antibiot (Tokyo). 1981 Mar;34(3):346-9
pubmed: 7275814
Chem Rev. 2006 Sep;106(9):3963-86
pubmed: 16967926
Cancer Res. 2000 May 1;60(9):2504-11
pubmed: 10811132
Appl Microbiol Biotechnol. 1999 Oct;52(4):455-63
pubmed: 10570792
Org Lett. 2021 Jul 2;23(13):4976-4980
pubmed: 34110162
Chem Sci. 2022 Oct 15;13(43):12776-12781
pubmed: 36519065
Nat Prod Rep. 2014 Apr;31(4):563-94
pubmed: 24595879
Org Lett. 2017 Aug 4;19(15):3998-4001
pubmed: 28718654
J Nat Prod. 2016 Oct 28;79(10):2446-2454
pubmed: 27690254
J Org Chem. 2022 Jan 21;87(2):1110-1123
pubmed: 34995058
Org Lett. 2021 Feb 5;23(3):676-681
pubmed: 33325708
Mol Divers. 2022 Feb;26(1):647-689
pubmed: 33609222
Chem Rev. 2011 May 11;111(5):3076-154
pubmed: 21434642
J Am Chem Soc. 2022 Nov 2;144(43):19953-19972
pubmed: 36269121
Angew Chem Int Ed Engl. 2020 May 4;59(19):7419-7424
pubmed: 32096300
Chemistry. 2022 Dec 20;28(71):e202202383
pubmed: 36081382
Org Biomol Chem. 2022 May 26;20(20):4135-4140
pubmed: 35510627
Fortschr Chem Org Naturst. 1989;55:1-35
pubmed: 2687139
Chemistry. 2013 Jul 08;19(28):9319-24
pubmed: 23703738
Acc Chem Res. 2021 Apr 20;54(8):1891-1908
pubmed: 33792282
Chemistry. 2021 Apr 26;27(24):7085-7089
pubmed: 33769622
Angew Chem Int Ed Engl. 2022 Jan 17;61(3):e202114514
pubmed: 34820990
Molecules. 2023 Mar 17;28(6):
pubmed: 36985698
Nat Prod Rep. 2016 Feb;33(2):141-9
pubmed: 26584443
Angew Chem Int Ed Engl. 2013 Aug 26;52(35):9097-108
pubmed: 23893491
Adv Synth Catal. 2013 Nov 11;355(16):3095-3118
pubmed: 24971045
Org Lett. 2014 Oct 17;16(20):5262-5
pubmed: 25192355
Chem Rev. 2008 Oct;108(10):4295-327
pubmed: 18817355
J Antibiot (Tokyo). 1979 Oct;32(10):1069-71
pubmed: 528370
Chem Sci. 2021 Jun 28;12(30):10259-10265
pubmed: 34377413
Nat Prod Rep. 2007 Apr;24(2):327-57
pubmed: 17390000
J Am Chem Soc. 2011 Feb 9;133(5):1428-37
pubmed: 21210688
J Am Chem Soc. 2020 Apr 22;142(16):7306-7311
pubmed: 32285674
J Am Chem Soc. 2022 Mar 30;144(12):5268-5273
pubmed: 35297610
Planta Med. 1998 Apr;64(3):208-11
pubmed: 9581515
Angew Chem Int Ed Engl. 2021 Mar 29;60(14):7893-7899
pubmed: 33448619
Nat Prod Rep. 2018 Jan 25;35(1):75-104
pubmed: 29354841
ACS Omega. 2021 Apr 30;6(18):11943-11953
pubmed: 34056349
Angew Chem Int Ed Engl. 2011 Mar 28;50(14):3219-23
pubmed: 21374771
Nat Prod Rep. 1992 Aug;9(4):289-312
pubmed: 1522977
J Antibiot (Tokyo). 2001 Feb;54(2):153-6
pubmed: 11302488
Angew Chem Int Ed Engl. 2015 Aug 24;54(35):10145-8
pubmed: 26031409
J Antibiot (Tokyo). 1966 Mar;19(2):51-5
pubmed: 5952891
Org Lett. 2020 Jun 5;22(11):4073-4077
pubmed: 32391700
Science. 2015 Mar 6;347(6226):1064-6
pubmed: 25745145
J Am Chem Soc. 2021 Jun 9;143(22):8261-8265
pubmed: 34043906
Org Lett. 2022 May 6;24(17):3254-3258
pubmed: 35467884
Appl Environ Microbiol. 1999 Jan;65(1):307-10
pubmed: 9872797
J Antibiot (Tokyo). 1995 Dec;48(12):1446-52
pubmed: 8557602
J Nat Prod. 2014 Nov 26;77(11):2459-64
pubmed: 25353976
Org Lett. 2021 Sep 3;23(17):6972-6976
pubmed: 34397211
Org Lett. 2020 Oct 16;22(20):8018-8022
pubmed: 32991182
Nat Prod Rep. 2010 Nov;27(11):1618-29
pubmed: 20877901
P T. 2015 Apr;40(4):277-83
pubmed: 25859123
Org Lett. 2009 Nov 19;11(22):5166-9
pubmed: 19873990
Angew Chem Int Ed Engl. 2015 Aug 24;54(35):10149-54
pubmed: 26179970
Mar Drugs. 2019 Dec 03;17(12):
pubmed: 31816961
J Antibiot (Tokyo). 2018 Nov;71(12):992-999
pubmed: 30127422
Org Lett. 2010 May 7;12(9):2158-61
pubmed: 20387889
Molecules. 2019 Aug 22;24(17):
pubmed: 31443344
Angew Chem Int Ed Engl. 2013 Jul 22;52(30):7822-4
pubmed: 23776159
J Antibiot (Tokyo). 1981 Aug;34(8):1075-7
pubmed: 7332707
J Org Chem. 2020 Apr 3;85(7):4637-4647
pubmed: 32162521
J Antibiot (Tokyo). 2017 Aug 02;:
pubmed: 28765588
J Am Chem Soc. 2021 Mar 24;143(11):4379-4386
pubmed: 33705657
J Am Chem Soc. 2003 Jan 15;125(2):350-1
pubmed: 12517144
Pak J Pharm Sci. 2019 Sep;32(5(Supplementary)):2215-2222
pubmed: 31894047
J Am Chem Soc. 2012 Sep 12;134(36):14973-81
pubmed: 22891640
Nat Prod Rep. 2013 Jul;30(7):1028-65
pubmed: 23736383
Nat Rev Cancer. 2004 Apr;4(4):253-65
pubmed: 15057285
Molecules. 2020 Jan 17;25(2):
pubmed: 31963564
Planta Med. 1988 Apr;54(2):117-20
pubmed: 3406169
Chembiochem. 2013 Jan 2;14(1):49-52
pubmed: 23172726
Org Lett. 2021 Sep 17;23(18):7069-7073
pubmed: 34459614
Org Lett. 2022 Jun 24;24(24):4305-4309
pubmed: 35536108
J Am Chem Soc. 2020 Sep 2;142(35):15116-15126
pubmed: 32786797