RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2021; 53(21): 4110-4116
DOI: 10.1055/a-1532-8656
DOI: 10.1055/a-1532-8656
paper
Total Synthesis of Methyl 1,5,8-Trimethoxy-1H-isochromene-3-carboxylate and Its Derivatives via Palladium-Catalyzed Annulation of 2-Alkynylbenzaldehydes
We are grateful to the following agencies for financial support of this work: the Natural Sciences and Engineering Research Council of Canada (NSERC; Idea to Innovation and Discovery Grants), the Canada Research Chair Program, the Canada Foundation for Innovation (CFI), TDC Research, Inc., the TDC Research Foundation, the Ontario Partnership for Innovation and Commercialization (OPIC), and The Advanced Biomanufacturing Centre (Brock University).
Abstract
A 7-step total synthesis of methyl 1,5,8-trimethoxy-1H-isochromene-3-carboxylate and a 5-step synthesis of its C-3 derivatives are reported. Sonogashira coupling of 2-halobenzaldehydes with terminal acetylenes was employed to access 2-alkynylbenzaldehydes, which underwent a Pd-catalyzed annulation to afford the corresponding isochromene-containing products.
Key words
2-alkynylbenzaldehydes - antitumor agents - isochromene annulations - palladium catalysis - total synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1532-8656.
- Supporting Information
Publikationsverlauf
Eingereicht: 30. April 2021
Angenommen nach Revision: 21. Juni 2021
Accepted Manuscript online:
21. Juni 2021
Artikel online veröffentlicht:
27. Juli 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Hayashi T, Smith FT, Lee KH. J. Med. Chem. 1987; 30: 2005
- 1b Hari L, De Buyck LF, De Pootert HL. Phytochemistry 1991; 30: 1726
- 1c Solis PN, Lang’at C, Gupta MP, Kirby GC, Warhurst DC, Phillipson JD. Planta Med. 1995; 61: 62
- 1d Kongue Tatong MD, Talontsi FM, Abdel Rahim HM. D, Islam MT, Oswald RB, Laatsch H. Tetrahedron Lett. 2014; 55: 4057
- 1e Tichenor MS, Boger DL. Nat. Prod. Rep. 2008; 25: 220
- 1f Asai T, Yamamoto T, Chung YM, Chang FR, Wu YC, Yamashita K, Oshima Y. Tetrahedron Lett. 2012; 53: 277
- 1g Braca A, Bader A, De Tommasi N. Plant and Fungi 3,4-Dihydroisocoumarins: Structures, Biological Activity, and Taxonomic Relationships, Vol. 37. Elsevier; Amsterdam: 2012
- 2a He H, Yang HY, Luckman SW, Roll DM, Carter GT. J. Antibiot. 2002; 55: 1072
- 2b Bieber B, Nuske J, Ritzau M, Grafe U. J. Antibiot. 1998; 51: 381
- 3a Shimbashi A, Nishiyama S. Tetrahedron Lett. 2007; 48: 1545
- 3b Oja T, Palmu K, Lehmussola H, Leppäranta O, Hännikäinen K, Niemi J, Mäntsälä P, Metsä-Ketelä M. Chem. Biol. 2008; 15: 1046
-
4
Attardo G,
Wang W,
Breining T,
Li T,
St-Denis Y,
Kraus J.-L.
Int. Patent WO9512588, 1995
- 5a Bacchi A, Costa M, Della Cà N, Fabbricatore M, Fazio A, Gabriele B, Nasi C, Salerno G. Eur. J. Org. Chem. 2004; 574
- 5b Wei LL, Wei LM, Pan WB, Wu MJ. Synlett 2004; 1497
- 5c Asao N, Nogami T, Takahashi K, Yamamoto Y. J. Am. Chem. Soc. 2002; 124: 764
- 5d Mondal S, Nogami T, Asao N, Yamamoto Y. J. Org. Chem. 2003; 68: 9496
- 5e Tang RY, Li JH. Chem. Eur. J. 2010; 16: 4733
- 5f Nakamura I, Mizushima Y, Gridnev ID, Yamamoto Y. J. Am. Chem. Soc. 2005; 127: 9844
- 5g Gabriele B, Salerno G, Fazio A, Pittelli R. Tetrahedron 2003; 59: 6251
- 5h Mutter R, Campbell IB, de la Nava EM. M, Merritt AT, Wills M. J. Org. Chem. 2001; 66: 3284
- 5i Zhang J, Han X. Adv. Synth. Catal. 2014; 356: 2465
- 6a Barluenga J, Vázquez-Villa H, Ballesteros A, González JM. J. Am. Chem. Soc. 2003; 125; 9028
- 6b Tomás-Mendivil E, Starck J, Ortuno JC, Michelet V. Org. Lett. 2015; 17: 6126
- 6c Yue D, Della Cà N, Larock RC. Org. Lett. 2004; 6: 1581
- 6d Yamamoto Y. J. Org. Chem. 2008; 73: 5210
- 6e Godet T, Bosson J, Belmont P. Synlett 2005; 2786
- 7 Nardangeli N, Topolovčan N, Simionescu R, Hudlický T. Eur. J. Org. Chem. 2020; 227
- 8 Saxena A, Perez F, Krische MJ. Angew. Chem. Int. Ed. 2016; 55: 1493
- 9a Yoneda N, Matsuoka S, Miyaura N, Fukuhara T, Suzuki A. Bull. Chem. Soc. Jpn. 1990; 63: 2124
- 9b Götzinger AC, Michaelis CS, Müller TJ. J. Dyes Pigm. 2017; 143: 308
- 9c Lakshminarayana B, Chakraborty J, Satyanarayana G, Subrahmanyam C. RSC Adv. 2018; 8: 21030
- 9d Yoneda N, Matsuoka S, Miyaura N, Fukuhara T, Suzuki A. Bull. Chem. Soc. Jpn. 1990; 63: 2124
- 10 Wenkert E, Adams KA. H, Leicht CL. Can. J. Chem. 1963; 41: 1844
- 11 Eckert T, Ipaktschi J. Synth. Commun. 1998; 28: 327
- 12 Saxena A, Perez F, Krische MJ. Angew. Chem. Int. Ed. 2016; 55: 1493
- 13 Ronald RC, Lansinger JM, Lillie TS, Wheeler CJ. J. Org. Chem. 1982; 47: 2541