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Synthesis 2025; 57(11): 1833-1847
DOI: 10.1055/a-2501-4796
DOI: 10.1055/a-2501-4796
feature
A Revised Protecting Group Strategy Enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia
This work was supported by Ph.D. scholarship (2018–2021) for GK from the German Academic Exchange Service (DAAD, grant number 57381412).
Abstract
Three bioactive prenylated isoflavone natural products were synthesized for the first time, using a combination of Pd-catalyzed Suzuki–Miyaura coupling for installing the B-ring, microwave-promoted Claisen rearrangement of allyl ethers, and Ru-catalyzed olefin cross metathesis for obtaining the prenyl substituents. Careful consideration of the protecting group strategy turned out to be vital for the success of these total syntheses.
Key words
isoflavones - Suzuki coupling - Claisen rearrangement - olefin metathesis - protecting groupsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2501-4796.
- Supporting Information
Publikationsverlauf
Eingereicht: 12. November 2024
Angenommen nach Revision: 12. Dezember 2024
Accepted Manuscript online:
12. Dezember 2024
Artikel online veröffentlicht:
21. Januar 2025
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References
- 1 Pan S.-Y, Litscher G, Gao S.-H, Zhou S.-F, Yu Z.-L, Chen H.-Q, Zhang S.-F, Tang M.-K, Sun J.-N, Ko K.-M. J. Evid. Based Complementary Altern. Med. 2014; 525340
- 2 Zhang M, Moalin M, Haenen GR. M. M. Int. J. Mol. Sci. 2019; 20: 2333
- 3 Accessed Oct 17, 2024: WHO Traditional Medicine Strategy 2002–2005 . World Health Organization; Geneva: 2002. https://www.who.int/publications/i/item/WHO-EDM-TRM-2002.1
- 4 Accessed Oct 17, 2024: WHO Traditional Medicine Strategy 2014–2023 . World Health Organization; Geneva: 2013. https://www.who.int/publications/i/item/9789241506096
- 5 Willcox ML, Cosentino MJ, Pink R, Wayling S, Bodeker G. Trends Parasitol. 2001; 17: 58
- 6 Pirintsos S, Panagiotopoulos A, Bariotakis M, Daskalakis V, Lionis C, Sourvinos G, Karakasiliotis I, Kampa M, Castanas E. Molecules 2022; 27: 4060
- 7 Kayser O. Planta Med. 2018; 84: 834
- 8 Blakemore DC, Castro L, Churcher I, Rees DC, Thomas AW, Wilson DM, Wood A. Nat. Chem. 2018; 10: 383
- 9 Derese S, Barasa L, Akala HM, Yusuf AO, Kamau E, Heydenreich M, Yenesew A. Phytochem. Lett. 2014; 8: 69
- 10 Muiva-Mutisya L, Macharia B, Heydenreich M, Koch A, Akala HM, Derese S, Omosa LK, Yusuf AO, Kamau E, Yenesew A. Phytochem. Lett. 2014; 10: 179
- 11 Deyou T, Gumula I, Pang F, Gruhonjic A, Mumo M, Holleran J, Duffy S, Fitzpatrick PA, Heydenreich M, Landberg G, Derese S, Avery V, Rissanen K, Erdélyi M, Yenesew A. J. Nat. Prod. 2015; 78: 2932
- 12 Deyou T, Marco M, Heydenreich M, Pan F, Gruhonjic A, Fitzpatrick PA, Koch A, Derese S, Pelletier J, Rissanen K, Yenesew A, Erdélyi M. J. Nat. Prod. 2017; 80: 2060
- 13 Marco M, Deyou T, Gruhonjic A, Holleran J, Duffy S, Heydenreich M, Firtzpatrick PA, Landberg G, Koch A, Derese S, Pelletier J, Avery VM, Erdélyi M, Yenesew A. Phytochem. Lett. 2017; 21: 216
- 14 Buyinza D, Yang LJ, Derese S, Ndakala A, Coghi P, Heydenreich M, Wong VK. W, Möller HM, Yenesew A. Nat. Prod. Res. 2019; 35: 2744
- 15 Atilaw Y, Muiva-Mutisya L, Bogaerts J, Duffy S, Valkonen A, Heydenreich M, Avery VM, Rissanen K, Erdélyi M, Yenesew A. J. Nat. Prod. 2020; 83: 2390
- 16 Nchiozem-Ngnitedem V.-A, Omosa LK, Derese S, Tane P, Heydenreich M, Spiteller M, Seo E.-J, Efferth T. Phytochem. Lett. 2020; 36: 80
- 17 Oloya B, Namukobe J, Heydenreich M, Ssengooba W, Schmidt B, Byamukama R. Nat. Prod. Commun. 2021; 16
- 18 Oloya B, Namukobe J, Heydenreich M, Ssengooba W, Martin J, Möller HM, Schmidt B, Byamukama R. Phytochem. Lett. 2023; 54: 107
- 19 Al-Maharik N. Nat. Prod. Rep. 2019; 36: 1156
- 20 Donnelly DM. X, Boland GM. Nat. Prod. Rep. 1995; 12: 321
- 21 Veitch NC. Nat. Prod. Rep. 2007; 24: 417
- 22 Crombie L, Whiting DA. Phytochemistry 1998; 49: 1479
- 23 Gessler MC, Nkunya MH. H, Mwasumbi LB, Heinrich M, Tanner M. Acta Trop. 1994; 56: 65
- 24 Andayi AW, Yenesew A, Derese S, Midiwo JO, Gitu PM, Jondiko OJ. I, Akala H, Liyala P, Wangui J, Waters NC, Heydenreich M, Peter MG. Planta Med. 2006; 72: 187
- 25 Xu S, Kang A, Tian Y, Li X, Qin S, Yang R, Guo Y. ACS Infect. Dis. 2024; 10: 3086
- 26 Kwesiga G, Kelling A, Kersting S, Sperlich E, von Nickisch-Rosenegk M, Schmidt B. J. Nat. Prod. 2020; 83: 3445
- 27 Kwesiga G. Ph.D. Dissertation. University of Potsdam; Potsdam: 2022
- 28 Kwesiga G, Sperlich E, Schmidt B. J. Org. Chem. 2021; 86: 10699
- 29 Kwesiga G, Greese J, Kelling A, Sperlich E, Schmidt B. J. Org. Chem. 2023; 88: 1649
- 30 Liu Y.-P, Guo J.-M, Yan G, Zhang M.-M, Zhang W.-H, Qiang L, Fu Y.-H. J. Agric. Food Chem. 2019; 67: 4817
- 31 Nchiozem-Ngnitedem V.-A, Sperlich E, Matieta VY, Ngnouzouba Kuete JR, Kuete V, Omer EA, Efferth T, Schmidt B. J. Nat. Prod. 2023; 86: 1520
- 32 Ma S, Huang Y, Zhao Y, Du G, Feng L, Huang C, Li Y, Guo F. Phytochem. Lett. 2016; 16: 213
- 33 Chen C.-H, Hwang T.-L, Chen L.-C, Chang T.-H, Wei C.-S, Chen J.-J. Phytochemistry 2017; 143: 186
- 34 Xu Q, Zhang Y, He Z, Liu Z, Zhang Y, Xu W, Yang X. Phytochemistry 2022; 196: 113085
- 35 Chen L, Chen S, Sun P, Liu X, Zhan Z, Wang J. Chin. Med. 2023; 18: 4
- 36 Fei W.-T, Zhang J.-J, Tang R.-Y, Yue N, Zhou X, Wang L.-Y. Phytochem. Lett. 2020; 39: 64
- 37 Hakamatsuka T, Ebizuka Y, Sankawa U. Phytochemistry 1991; 30: 1481
- 38 Iinuma M, Tanaka T, Mizuno M, Yamamoto H, Kobayashi Y, Yonemori S. Chem. Pharm. Bull. 1992; 40: 2749
- 39 Nkengfack AE, Vouffo TW, Vardamides JC, Kouam J, Fomum ZT, Meyer M, Sterner O. Phytochemistry 1997; 46: 573
- 40 Nkengfack AE, Waffo AK, Azebaze GA, Fomum ZT, Meyer M, Bodo B, van Heerden FR. J. Nat. Prod. 2000; 63: 855
- 41 Pistelli L, Noccioli C, Appendino G, Bianchi F, Sterner O, Ballero M. Phytochemistry 2003; 64: 595
- 42 Yin S, Fan C.-Q, Wang Y, Dong L, Yue J.-M. Bioorg. Med. Chem. 2004; 12: 4387
- 43 Schmidt B, Riemer M, Schilde U. Eur. J. Org. Chem. 2015; 7602
- 44 Żukowska K, Grela K. Cross Metathesis . In Comprehensive Organic Synthesis, 2nd ed., Vol. 5. Knochel P, Molander GA. Elsevier; Amsterdam: 2014: 1257-1301
- 45 Chatterjee AK, Sanders DP, Grubbs RH. Org. Lett. 2002; 4: 1939
- 46 Scholl M, Ding S, Lee CW, Grubbs RH. Org. Lett. 1999; 1: 953
- 47 Fürstner A, Langemann K. Synthesis 1997; 792
- 48 Schultze C, Schmidt B. J. Org. Chem. 2018; 83: 5210
- 49 Chi X.-Q, Zi C.-T, Li H.-M, Yang L, Lv Y.-F, Li J.-Y, Hou B, Ren F.-C, Hu J.-M, Zhou J. RSC Adv. 2018; 8: 41377
- 50 Narender T, Papi Reddy K, Kumar B. Tetrahedron Lett. 2008; 49: 4409
- 51 Gammill RB. Synthesis 1979; 901
- 52 Gentry EJ, Telikepalli H, Srinivas P, Mitscher LA. Comb. Chem. High Throughput Screen. 2003; 6: 139
- 53 Spadafora M, Postupalenko VY, Shvadchak VV, Klymchenko AS, Mély Y, Burger A, Benhida R. Tetrahedron 2009; 65: 7809
- 54 Kadu BS. Catal. Sci. Technol. 2021; 11: 1186
- 55 Selepe MA, Van Heerden FR. Molecules 2013; 18: 4739
- 56 Ciesielski P, Metz P. Nat. Commun. 2020; 11: 3091
- 57 Kocienski PJ. Protecting Groups . Thieme; Stuttgart: 2003
- 58 Lam LK. T, Farhat K. Org. Prep. Proced. Int. 1978; 10: 79
- 59 Kraus JM, Gits HC, Silverman RB. Tetrahedron Lett. 2012; 53: 1319
- 60 Goux C, Massacret M, Lhoste P, Sinou D. Organometallics 1995; 14: 4585
- 61 Haight AR, Stoner EJ, Peterson MJ, Grover VK. J. Org. Chem. 2003; 68: 8092
- 62 Schmidt B, Nave S. Adv. Synth. Catal. 2006; 348: 531
- 63 Abdel-Magid AF, Cohen JH, Maryanoff CA, Shah RD, Villani FJ, Zhang F. Tetrahedron Lett. 1998; 39: 3391
- 64 Pedersen DS, Rosenbohm C. Synthesis 2001; 2431
- 65 CCDC 2394462 (10) and 2394463 (19) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
- 66 Xiao G, Li G, Chen L, Zhang Z, Yin J.-J, Wu T, Cheng Z, Wei X, Wang Z. J. Chromatogr., A 2010; 1217: 5470