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Synthesis 2021; 53(19): 3630-3638
DOI: 10.1055/a-1508-9541
DOI: 10.1055/a-1508-9541
paper
Synthesis of Nilotinin M3: An Ellagitannin Containing an Isodehydrodigalloyl Group
A part of this work was financially supported by The Hokuriku Bank Grant-in Aid for Young Scientists for H.A.

Abstract
Total synthesis of nilotinin M3, which is a member of the ellagitannin family of natural products containing an isodehydrodigalloyl (isoDHDG) group, was achieved using the Ullmann reaction to construct a highly functionalized diaryl ether.
Key words
total synthesis - ellagitannin - highly functionalized diaryl ether - Ullmann condensation - isodehydrodigalloyl groupSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1508-9541.
- Supporting Information
Publication History
Received: 22 March 2021
Accepted after revision: 14 May 2021
Accepted Manuscript online:
14 May 2021
Article published online:
15 June 2021
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References
- 1a Miyamoto K, Kishi N, Koshiura R, Yoshida T, Hatano T, Okuda T. Chem. Pharm. Bull. 1987; 35: 814
- 1b Miyamoto K, Nomura M, Sasakura M, Matsui E, Koshiura R, Murayama T, Furukawa T, Hatano T, Yoshida T, Okuda T. Jpn. J. Cancer Res. 1993; 84: 99
- 1c Miyamoto K, Nomura M, Murayama T, Furukawa T, Hatano T, Yoshida T, Koshiura R, Okuda T. Biol. Pharm. Bull. 1993; 16: 379
- 2 Halvorsen BL, Holte K, Myhrstrad MC. W, Barikmo T, Hvattum E, Remberg SF, Wold AB, Haffner K, Baugerød H, Andersen LF, Moskaug O, Jacobs DR, Blomhoff R. J. Nutr. 2002; 132: 461
- 3 Yoshida T, Ito H, Hatano T, Kurata M, Nakanishi T, Inada A, Murata H, Inatomi Y, Matsuura N, Ono K, Nakane H, Nodo M, Lang FA, Murata J. Chem. Pharm. Bull. 1996; 44: 1436
- 4 Fukuchi K, Sakagami H, Okuda T, Hatano T, Tanuma S, Kitajima K, Inoue Y, Inoue S, Ichikawa S. Antiviral Res. 1989; 11: 285
- 5 Chemistry and Biology of Ellagitannins. An Underestimated Class of Bioactive Plant Polyphenols. Quideau S. World Scientific Publishing; Singapore: 2009
- 6 Nishioka I. Yakugaku Zasshi 1983; 103: 125
- 7a Quideau S, Feldman KS. Chem. Rev. 1996; 96: 475
- 7b Feldman KS, Sahasrabudhe S. J. Org. Chem. 1999; 64: 209
- 7c Pouységu L, Deffieux D, Malik G, Natangelo A, Quideau S. Nat. Prod. Rep. 2011; 28: 853 ; and references cited therein
- 7d Kasai Y, Michihata N, Nishimura H, Hirokane T, Yamada H. Angew. Chem. Int. Ed. 2012; 51: 8026
- 7e Yamada H, Ohara K, Ogura T. Eur. J. Org. Chem. 2013; 7872
- 7f Michihata N, Kaneko Y, Kasai Y, Tanigawa K, Hirokane T, Higasa S, Yamada H. J. Org. Chem. 2013; 78: 4319
- 7g Yamaguchi S, Hirokane T, Yoshida T, Tanaka T, Hatano T, Ito H, Nonaka G, Yamada H. J. Org. Chem. 2013; 78: 5410
- 7h Hirokane T, Hirata Y, Ishimoto T, Nishii K, Yamada H. Nat. Commun. 2014; 5: 3478
- 7i Hirokane T, Ikeuchi K, Yamada H. Eur. J. Org. Chem. 2015; 7352
- 7j Takeuchi H, Mishiro K, Ueda Y, Fujimori Y, Furuta T, Kawabata T. Angew. Chem. Int. Ed. 2015; 54: 6177
- 7k Richieu A, Peixoto PA, Pouységu L, Deffieux D, Quideau S. Angew. Chem. Int. Ed. 2017; 56: 13833
- 7l Kaneko Y, Wakamori S, Ikeuchi K, Ohara K, Tanaka T, Yamada H. Synthesis 2017; 49: 5003
- 7m Takeuchi H, Ueda Y, Furuta T, Kawabata T. Chem. Pharm. Bull. 2017; 65: 25
- 7n Abe H, Ogura D, Horino Y. Heterocycles 2017; 95: 131
- 7o Abe H, Kato Y, Imai H, Horino Y. Heterocycles 2018; 97: 1237
- 7p Ikeuchi K, Ueji T, Matsumoto S, Wakamori S, Yamada H. Eur. J. Org. Chem. 2020; 2077
- 7q Wakamori S, Matsumoto S, Kusuki R, Ikeuchi K, Yamada H. Org. Lett. 2020; 22: 3392
- 7r Abe H, Imai H, Ogura D, Horino Y. Heterocycles 2020; 101: 524
- 8 Orabi MA. A, Taniguchi S, Yoshimura M, Yoshida T, Hatano T. Heterocycles 2010; 80: 463
- 9a Lin JH, Ishimatsu M, Tanaka T, Nonaka G, Nishioka I. Chem. Pharm. Bull. 1990; 38: 1844
- 9b Feldman KS, Quideau S, Appel HM. J. Org. Chem. 1996; 61: 6656
- 9c Shioe K, Ishikura S, Horino Y, Abe H. Chem. Pharm. Bull. 2013; 61: 1308
- 9d Abe H, Ishikura S, Horino Y. Synlett 2016; 27: 859
- 9e Konishi H, Hirokane T, Hashimoto H, Ikeuchi K, Matsumoto S, Wakamori S, Yamada H. Chem. Commun. 2020; 56: 3991
- 9f Hashimoto H, Ishimoto T, Konishi H, Hirokane T, Wakamori S, Ikeuchi K, Yamada H. Org. Lett. 2020; 22: 6729
- 9g Imai H, Koyama R, Horino Y, Abe H. Chem. Pharm. Bull. 2021; 69: 298
- 10a Ullmann F. Ber. Dtsch. Chem. Ges. 1904; 37: 853
- 10b Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
- 10c Gorginpour F, Zali-Boeini H. Mol. Catal. 2021; 504: 111460
- 10d Ray R, Hartwig JF. Angew. Chem. Int. Ed. 2021; 60: 8203
- 11 Lu X.-A, Chou C.-H, Wang C.-C, Hung S.-C. Synlett 2003; 1364
- 12 Ren Y, Himmelderik K, Chen X. J. Med. Chem. 2006; 49: 2829
- 13a Feldman KS, Lawlor MD, Saahasrabudhe K. J. Org. Chem. 2000; 65: 8011
- 13b Feldman KS, Lawlor MD. J. Am. Chem. Soc. 2000; 122: 7396
-
14 Although we attempted some general hydrolysis and aminolysis conditions, liberation of compound 10 or its analogue was detected in all cases.
- 15 Nishiyama K, Maeda M, Yanagisawa K, Nagase R, Komura H, Iwashita T, Yamagaki T, Kusumoto S, Tokuda H, Shimamoto K. Nat. Commun. 2012; 3: 1260