Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002-2020).


Journal

Chemical reviews
ISSN: 1520-6890
Titre abrégé: Chem Rev
Pays: United States
ID NLM: 2985134R

Informations de publication

Date de publication:
09 08 2023
Historique:
medline: 10 8 2023
pubmed: 10 7 2023
entrez: 10 7 2023
Statut: ppublish

Résumé

The tetrahydroisoquinoline (THIQ) natural products constitute one of the largest families of alkaloids and exhibit a wide range of structural diversity and biological activity. Ranging from simple THIQ natural products to complex trisTHIQ alkaloids such as the ecteinascidins, the chemical syntheses of these alkaloids and their analogs have been thoroughly investigated due to their intricate structural features and functionalities, as well as their high therapeutic potential. This review describes the general structure and biosynthesis of each family of THIQ alkaloids as well as recent advancements of the total synthesis of these natural products from 2002 to 2020. Recent chemical syntheses that have emerged harnessing novel, creative synthetic design, and modern chemical methodology will be highlighted. This review will hopefully serve as a guide for the unique strategies and tools used in the total synthesis of THIQ alkaloids, as well as address the longstanding challenges in their chemical and biosynthesis.

Identifiants

pubmed: 37429001
doi: 10.1021/acs.chemrev.3c00054
pmc: PMC10416225
doi:

Substances chimiques

Alkaloids 0
Tetrahydroisoquinolines 0
Biological Products 0

Types de publication

Journal Article Review Research Support, Non-U.S. Gov't Research Support, N.I.H., Extramural

Langues

eng

Sous-ensembles de citation

IM

Pagination

9447-9496

Subventions

Organisme : NIGMS NIH HHS
ID : R35 GM145239
Pays : United States

Références

J Org Chem. 2004 Apr 16;69(8):2737-40
pubmed: 15074921
Org Lett. 2009 Nov 19;11(22):5230-3
pubmed: 19860384
J Nat Prod. 2010 Aug 27;73(8):1427-30
pubmed: 20617818
Tetrahedron Lett. 1969 Apr;(19):1515-7
pubmed: 5794441
J Org Chem. 2011 Jun 17;76(12):5036-41
pubmed: 21563765
Science. 2019 Jan 18;363(6424):270-275
pubmed: 30573544
J Org Chem. 2015 Feb 6;80(3):1957-63
pubmed: 25569446
Org Lett. 2015 Mar 6;17(5):1134-7
pubmed: 25710592
Org Biomol Chem. 2020 Apr 29;18(16):3047-3068
pubmed: 32091528
Angew Chem Int Ed Engl. 2014 Dec 22;53(52):14555-8
pubmed: 25348493
J Am Chem Soc. 2002 Jun 12;124(23):6552-4
pubmed: 12047173
J Org Chem. 2016 May 20;81(10):4039-47
pubmed: 27019081
Chem Biol. 2013 Dec 19;20(12):1523-35
pubmed: 24269153
Angew Chem Int Ed Engl. 2006 Dec 4;45(47):8028-32
pubmed: 17099922
Org Lett. 2020 Jun 5;22(11):4489-4493
pubmed: 32437173
J Am Chem Soc. 2013 Sep 18;135(37):13684-7
pubmed: 24001124
Org Lett. 2022 Jan 14;24(1):127-131
pubmed: 34882414
Org Lett. 2006 Nov 9;8(23):5311-3
pubmed: 17078705
Alkaloids Chem Biol. 2005;62:1-75
pubmed: 16265921
Chem Commun (Camb). 2002 Jun 7;(11):1159-68
pubmed: 12109065
J Org Chem. 2002 Feb 22;67(4):1290-6
pubmed: 11846676
Chemistry. 2012 Sep 3;18(36):11192-5
pubmed: 22848018
Mol Microbiol. 2005 Apr;56(1):144-54
pubmed: 15773985
Proc Natl Acad Sci U S A. 2021 Dec 21;118(51):
pubmed: 34903659
J Am Chem Soc. 2018 Aug 29;140(34):10705-10709
pubmed: 30113836
J Biol Chem. 1995 Oct 13;270(41):24475-81
pubmed: 7592663
Org Biomol Chem. 2009 May 7;7(9):1963-79
pubmed: 19590794
J Antibiot (Tokyo). 1983 Oct;36(10):1279-83
pubmed: 6417094
Angew Chem Int Ed Engl. 2016 Nov 7;55(46):14306-14309
pubmed: 27735107
J Org Chem. 2021 Aug 20;86(16):11107-11116
pubmed: 33770435
J Org Chem. 2011 Dec 2;76(23):9777-84
pubmed: 22004161
Molecules. 2008 Nov 28;13(12):2935-47
pubmed: 19043347
J Antibiot (Tokyo). 1988 Aug;41(8):993-8
pubmed: 2459096
J Am Chem Soc. 2008 Oct 15;130(41):13745-54
pubmed: 18798630
Org Lett. 2016 Aug 5;18(15):3862-5
pubmed: 27463125
Org Lett. 2006 Feb 16;8(4):657-9
pubmed: 16468735
J Antibiot (Tokyo). 1988 Jun;41(6):734-40
pubmed: 3403367
Org Lett. 2009 Dec 3;11(23):5558-61
pubmed: 19894720
Chem Commun (Camb). 2018 Nov 15;54(92):13018-13021
pubmed: 30394459
J Nat Prod. 2003 Nov;66(11):1441-6
pubmed: 14640515
Chem Pharm Bull (Tokyo). 2020;68(9):899-902
pubmed: 32879231
Tetrahedron. 2015 Feb 25;71(8):1227-1231
pubmed: 25691805
Angew Chem Int Ed Engl. 2007;46(21):3962-5
pubmed: 17437314
Org Lett. 2019 Mar 15;21(6):1828-1831
pubmed: 30775928
J Am Chem Soc. 2002 Mar 27;124(12):2951-6
pubmed: 11902886
J Org Chem. 2008 Dec 19;73(24):9594-600
pubmed: 18687003
J Am Chem Soc. 2005 Sep 14;127(36):12476-7
pubmed: 16144380
Chemistry. 2016 Jan 26;22(5):1800-4
pubmed: 26689172
J Org Chem. 2015 Oct 16;80(20):10033-40
pubmed: 26375603
J Am Chem Soc. 2008 Dec 24;130(51):17270-1
pubmed: 19035638
Top Curr Chem. 2012;309:33-66
pubmed: 21547687
Molecules. 2021 Oct 10;26(20):
pubmed: 34684698
Org Lett. 2006 Jul 20;8(15):3299-301
pubmed: 16836390
J Nat Prod. 2004 Jun;67(6):1023-8
pubmed: 15217287
J Org Chem. 2013 May 17;78(10):4985-92
pubmed: 23634947
J Med Chem. 1993 Jul 9;36(14):1938-46
pubmed: 8101572
Angew Chem Int Ed Engl. 2006 Mar 3;45(11):1754-9
pubmed: 16496274
J Org Chem. 2011 Jul 1;76(13):5283-94
pubmed: 21627169
J Am Chem Soc. 2005 Dec 7;127(48):16796-7
pubmed: 16316220
Arch Int Pharmacodyn Ther. 1985 Nov;278(1):53-60
pubmed: 3938207
Org Biomol Chem. 2016 Aug 14;14(30):7334-44
pubmed: 27405490
J Biol Chem. 2016 Nov 4;291(45):23416-23427
pubmed: 27634038
Tetrahedron Lett. 2007 May 21;48(21):3719-3722
pubmed: 19578531
J Bacteriol. 2008 Jan;190(1):251-63
pubmed: 17981978
Angew Chem Int Ed Engl. 2007;46(9):1517-20
pubmed: 17387658
Molecules. 2009 Feb 26;14(3):917-24
pubmed: 19255550
Chem Sci. 2017 Oct 1;8(10):7031-7037
pubmed: 29147530
Angew Chem Int Ed Engl. 2012 Sep 3;51(36):9169-72
pubmed: 22890756
Org Lett. 2002 Aug 8;4(16):2675-8
pubmed: 12153207
Org Lett. 2000 Aug 10;2(16):2545-8
pubmed: 10956543
J Nat Prod. 2013 Sep 27;76(9):1789-95
pubmed: 24070054
J Nat Prod. 1988 Jul;51(4):760-4
pubmed: 21401143
J Am Chem Soc. 2008 Jun 4;130(22):7148-52
pubmed: 18454525
Phytochemistry. 1999 Oct;52(3):373-82
pubmed: 10501023
Angew Chem Int Ed Engl. 2017 Jun 1;56(23):6613-6616
pubmed: 28470985
J Nat Prod. 2003 Aug;66(8):1136-9
pubmed: 12932144
Org Lett. 2003 Jun 12;5(12):2095-8
pubmed: 12790537
Angew Chem Int Ed Engl. 2016 Jun 1;55(23):6734-8
pubmed: 27111396
Nat Prod Rep. 2009 Mar;26(3):322-37
pubmed: 19240944
Chemistry. 2015 Nov 9;21(46):16379-82
pubmed: 26428413
Nat Chem Biol. 2010 Jun;6(6):408-10
pubmed: 20453862
Nat Microbiol. 2019 Jul;4(7):1149-1159
pubmed: 30936484
Org Lett. 2018 Aug 17;20(16):5044-5047
pubmed: 30079736
J Am Chem Soc. 2019 Jul 10;141(27):10883-10904
pubmed: 31184866
Chem Commun (Camb). 2004 Dec 21;(24):2874-5
pubmed: 15599450
J Am Chem Soc. 2006 Sep 13;128(36):11752-3
pubmed: 16953603
Chemistry. 2013 Jul 01;19(27):8875-83
pubmed: 23681666
Chem Sci. 2018 Oct 23;10(2):535-541
pubmed: 30713650
J Biol Chem. 2016 Nov 4;291(45):23403-23415
pubmed: 27573242
ACS Chem Biol. 2011 Nov 18;6(11):1244-56
pubmed: 21875091
Chem Pharm Bull (Tokyo). 2021;69(2):155-177
pubmed: 33518599
Chem Asian J. 2010 Oct 4;5(10):2192-8
pubmed: 20715192
J Org Chem. 2018 Dec 21;83(24):15110-15117
pubmed: 30451502
Org Lett. 2000 Apr 6;2(7):993-6
pubmed: 10768205
Fitoterapia. 2014 Jul;96:109-14
pubmed: 24769286
ChemistryOpen. 2018 Aug 07;7(10):764-771
pubmed: 30338201
Angew Chem Int Ed Engl. 2016 Jun 6;55(24):6915-8
pubmed: 27145193
Chemistry. 2008;14(22):6606-8
pubmed: 18561354
J Antibiot (Tokyo). 1983 Sep;36(9):1184-94
pubmed: 6630077
J Am Chem Soc. 2005 Apr 6;127(13):4596-8
pubmed: 15796524
J Am Chem Soc. 2003 Dec 10;125(49):15000-1
pubmed: 14653730
Science. 2014 Mar 14;343(6176):1216-20
pubmed: 24626923
J Org Chem. 2005 Nov 11;70(23):9486-94
pubmed: 16268624
Nat Commun. 2019 Jun 7;10(1):2507
pubmed: 31175289
Org Lett. 2015 Jul 17;17(14):3422-5
pubmed: 26125652
J Org Chem. 2015 Feb 6;80(3):2010-6
pubmed: 25584789
Chemistry. 2017 May 23;23(29):6993-6995
pubmed: 28378531
Chem Rev. 2002 May;102(5):1669-730
pubmed: 11996547
Angew Chem Int Ed Engl. 2018 Aug 20;57(34):11055-11059
pubmed: 29786941
Org Lett. 2013 Jul 19;15(14):3674-7
pubmed: 23841701
Chemistry. 2013 Jan 2;19(1):264-9
pubmed: 23180383
Nat Chem Biol. 2010 Apr;6(4):273-5
pubmed: 20228795
J Org Chem. 2017 Jan 20;82(2):1205-1217
pubmed: 27997804
Angew Chem Int Ed Engl. 2017 Jul 24;56(31):9116-9120
pubmed: 28561936
J Org Chem. 2017 Dec 1;82(23):12899-12907
pubmed: 29083182
J Am Chem Soc. 2006 Jan 11;128(1):87-9
pubmed: 16390134
Org Lett. 2019 Nov 15;21(22):9194-9197
pubmed: 31682131
Angew Chem Int Ed Engl. 2015 Nov 16;54(47):14187-9
pubmed: 26474300
J Am Chem Soc. 2007 Dec 19;129(50):15460-1
pubmed: 18034496
J Antibiot (Tokyo). 1986 Dec;39(12):1639-50
pubmed: 3818437
Org Lett. 2014 Oct 17;16(20):5282-5
pubmed: 25271381
Org Lett. 2014 Dec 5;16(23):6244-7
pubmed: 25423610
Future Med Chem. 2016 Jan;8(1):17-27
pubmed: 26689493
Bioorg Med Chem Lett. 2011 Mar 1;21(5):1419-21
pubmed: 21295980
Chemistry. 2017 Sep 7;23(50):12149-12152
pubmed: 28603842
Chem Pharm Bull (Tokyo). 2007 Jan;55(1):81-6
pubmed: 17202706
Mar Drugs. 2015 Aug 06;13(8):4915-33
pubmed: 26287215
Chemistry. 2016 May 17;22(21):7084-9
pubmed: 26990887
J Antibiot (Tokyo). 1977 Nov;30(11):1015-8
pubmed: 591455
Angew Chem Int Ed Engl. 2019 Mar 18;58(12):3972-3975
pubmed: 30689274
J Am Chem Soc. 2005 Sep 14;127(36):12684-90
pubmed: 16144418
Nat Prod Res. 2020 Jul;34(13):1891-1912
pubmed: 31226894
Org Lett. 2007 Oct 11;9(21):4223-6
pubmed: 17887692
Chem Rev. 2016 Oct 12;116(19):12369-12465
pubmed: 27680197
Cancer Chemother Pharmacol. 1988;22(3):197-200
pubmed: 3409454
Biochemistry. 1982 Feb 2;21(3):419-28
pubmed: 7066293
Chem Commun (Camb). 2003 Sep 7;(17):2112-3
pubmed: 13678157
J Org Chem. 2016 Oct 21;81(20):10062-10070
pubmed: 27689544
Curr Opin Chem Biol. 2012 Apr;16(1-2):142-9
pubmed: 22409961
J Org Chem. 2006 Nov 10;71(23):8761-6
pubmed: 17081004
J Org Chem. 2006 Sep 15;71(19):7391-402
pubmed: 16958534
J Biol Chem. 1985 Jan 10;260(1):344-8
pubmed: 3880741
J Org Chem. 2011 Jul 1;76(13):5363-8
pubmed: 21612294
Org Lett. 2020 Apr 17;22(8):3145-3148
pubmed: 32250124

Auteurs

Alexia N Kim (AN)

The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Aurapat Ngamnithiporn (A)

Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Bangkok 10210, Thailand.

Emily Du (E)

The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Brian M Stoltz (BM)

The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Articles similaires

Humans Osteoporosis Wnt Signaling Pathway Animals Osteoblasts
Humans Drug Monitoring Inflammatory Bowel Diseases Psoriasis Adult

Mitoepigenetics pathways and natural compounds: a dual approach to combatting hepatocellular carcinoma.

Abdulrahman Hatawsh, Roya Hadi Al-Haddad, Ukamaka Gladys Okafor et al.
1.00
Humans Carcinoma, Hepatocellular Liver Neoplasms Epigenesis, Genetic Biological Products

Natural compounds targeting miRNAs: a novel approach in oral cancer therapy.

Youssef A Doghish, Ahmed S Doghish, Sherif S Abdel Mageed et al.
1.00
Humans MicroRNAs Mouth Neoplasms Biological Products Gene Expression Regulation, Neoplastic

Classifications MeSH