Synthetic Study on Acremoxanthone A, Part 2: Model Study on the EFG Xanthone Moiety through a Nitrile Oxide Cycloaddition–S_NAr Sequence

Abstract

Toward a total synthesis of acremoxanthone A, we report a model study on the construction of the EFG ring system. The key steps include (1) an intermolecular 1,3-dipolar cycloaddition of an aryl nitrile oxide with a dienone, and (2) an S_NAr reaction for construction of the F ring.

Key words

natural products - aromatic polyketides - acremoxanthone A - isoxazoles - cycloaddition - S_NAr reaction

Publication History

Received: 24 October 2020

Accepted after revision: 04 November 2020

Accepted Manuscript online:
04 November 2020

Article published online:
02 December 2020

• References and Notes

• 1 Current address: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
• 2a Yamashita Y, Hirano Y, Takada A, Takikawa H, Suzuki K. Synthesis 2018; 50: 2490
• 2b Yamashita Y, Hirano Y, Takada A, Takikawa H, Suzuki K. Angew. Chem. Int. Ed. 2013; 52: 6658
• 2c Sato S, Sakata K, Hashimoto Y, Takikawa H, Suzuki K. Angew. Chem. Int. Ed. 2017; 56: 12608
• 2d Takahashi N, Kanayama T, Okuyama K, Kataoka H, Fukaya H, Suzuki K, Matsumoto T. Chem. Asian J. 2011; 6: 1752
• 3a Isaka M, Palasarn S, Auncharoen P, Komwijit S, Jones EB. G. Tetrahedron Lett. 2009; 50: 284
• 3b Madariaga-Mazón A, González-Andrade M, del Carmen González M, Glenn AE, Cerda-García-Rojas CM, Mata R. J. Nat. Prod. 2013; 76: 1454
• 3c Meléndez-González C, Murià-González MJ, Anaya AL, Hernández-Bautista BE, Hernández-Ortega S, González MC, Glenn AE, Hanlin RT, Macías-Rubalcava ML. Chem. Biodiversity 2015; 12: 133
• 3d Intaraudom C, Bunbamrung N, Dramae A, Boonyuen N, Komwijit S, Rachtawee P, Pittayakhajonwut P. Tetrahedron 2016; 72: 1415
• 4a Hertweck C. Angew. Chem. Int. Ed. 2009; 48: 4688
• 4b Das A, Khosla C. Acc. Chem. Res. 2009; 42: 631
• 4c Hertweck C, Luzhetskyy A, Rebets Y, Bechthold A. Nat. Prod. Rep. 2007; 24: 162
• 4d Zhou H, Li Y, Tang Y. Nat. Prod. Rep. 2010; 27: 839
• 5a Holmbo SD, Pronin SV. J. Am. Chem. Soc. 2018; 140: 5065
• 5b Kramer CS, Bräse S. Beilstein J. Org. Chem. 2013; 9: 1414
• 5c Kramer CS, Nieger M, Bräse S. Eur. J. Org. Chem. 2014; 2150
• 6a Stork G, Danishefsky S, Ohashi M. J. Am. Chem. Soc. 1967; 89: 5459
• 6b Kashima C. Heterocycles 1979; 12: 1343
• 6c Baraldi PG, Barco A, Benetti S, Pollini GP, Simoni D. Synthesis 1987; 857
• 7 Hirano Y, Tokudome K, Takikawa H, Suzuki K. Synlett 2017; 28: 214
• 8a Horne S, Rodrigo R. J. Org. Chem. 1990; 55: 4520
• 8b Casillas LK, Townsend CA. J. Org. Chem. 1999; 64: 4050
• 8c Shen C, Wu X.-F. Synlett 2016; 27: 1269
• 8d Hintermann L, Masuo R, Suzuki K. Org. Lett. 2008; 10: 4859
• 8e Masuo R, Ohmori K, Hintermann L, Yoshida S, Suzuki K. Angew. Chem. Int. Ed. 2009; 48: 3462
• 8f Barbero N, SanMartin R, Domínguez E. Tetrahedron 2009; 65: 5729
• 8g Takahashi N, Kanayama T, Okuyama K, Kataoka H, Fukaya H, Suzuki K, Matsumoto T. Chem. Asian J. 2011; 6: 1752
• 8h Wei X, Liang D, Wang Q, Meng X, Li Z. Org. Biomol. Chem. 2016; 14: 8821
• 8i Reichl KD, Smith MJ, Song MK, Johnson RP, Porco JA. Jr. J. Am. Chem. Soc. 2017; 139: 14053
• 9 Boivin R, Chiba K, Davis HA, Diepitro L, Du H, Eguchi Y, Fujita M, Gilbert S, Goto M, Harmange JC, Inoue A, Jiang Y, Kawada M, Kawai T, Kawakami Y, Kimura A, Kotake M, Kuboi Y, Lemelin C, Li X.-Y, Matsushima T, Mizui Y, Sakurai H, Schiller S, Shen Y, Spyvee M, Tanaka I, Wang Y, Yamamoto S, Yoneda N, Kobayashi S. WO 03/076424 A1, 2003
• 10a Bode JW, Hachisu Y, Matsuura T, Suzuki K. Tetrahedron Lett. 2003; 44: 3555
• 10b Takikawa H, Sato S, Seki R, Suzuki K. Chem. Lett. 2017; 46: 998
• 11 Carreño MC, González-López M, Urbano A. Angew. Chem. Int. Ed. 2006; 45: 2737
• 12 Although a direct assignment of the stereostructure of 9 was not possible, we believe that this is the correct structure on the basis of a closely related example, that is, the cycloaddition of dienone 4 with nitrile oxide XI (with an ortho-methoxy group instead of the fluorine atom in 5). The reaction of 4 with XI (CHCl₃, rt, 136 h) gave cycloadduct XII as a major isomer, relative structure of which was verified by single-crystal X-ray diffraction analysis; see: Hirano, Y., Ph.D. Thesis, Tokyo Institute of Technology, Japan, 2016. CCDC 2006584 contains the supplementary crystallographic data for compound XII. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
• 13 Adembri G, Giorgi G, Lampariello RL, Paoli ML, Sega A. J. Chem. Soc., Perkin Trans. 1 2000; 2649
• 14 Tanaka H, Yoshioka T. Chem. Lett. 1994; 953
• 15 Kashima C, Tsuda Y, Imada S, Nishino T. J. Chem. Soc., Perkin Trans. 1, 1980; 1866
• 16 Recrystallization of 14 from EtOAc and hexane gave single crystals that were subjected to X-ray diffraction analysis. CCDC 2006581contains the supplementary crystallographic data for this compound. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
• 17 Pb(OAc)₄ was not be applicable to the total synthesis, due to an incompatibility with the anthraquinone moiety.
• 18a Lepore SD, Schacht AL, Wiley MR. Tetrahedron Lett. 2002; 43: 8777
• 18b Katagiri N, Sato H, Kurimoto A, Okada M, Yamada A, Kaneko C. J. Org. Chem. 1994; 59: 8101
• 18c Baraldi PG, Barco A, Benetti S, Moroder F, Pollini GP, Simoni D. J. Org. Chem. 1983; 48: 1297
• 19a Pass M, Bolton RE, Coote SJ, Finch H, Hindley S, Lowdon A, McDonald Es, McLaren J, Owen M, Pegg NA, Mooney CJ, Tang C.-M, Parry S, Patel C. Bioorg. Med. Chem. Lett. 1999; 431
• 19b Rahimizadeh M, Pordel M, Bakavoli M, Rezaeian S, Eshghi H. Can. J. Chem. 2009; 87: 724
• 19c Chiacchio U, Corsaro A, Pistarà V, Rescifina A, Romeo G, Romeo R. Tetrahedron 1996; 52: 7875
• 20a Xia X.-F, Zhu S.-L, Gu Z, Wang H, Li W, Liu X, Liang Y.-M. J. Org. Chem. 2015; 80: 5572
• 20b Nitta M, Kobayashi T. J. Chem. Soc., Perkin Trans. 1 1985; 1401
• 21a Koelle U. J. Organomet. Chem. 1977; 133: 53
• 21b van Assema SG. A, de Kanter FJ. J, Schakel M, Lammertsma K. Organometallics 2006; 25: 5286
• 21c Coco S, Cordovilla C, Domínguez C, Donnio B, Espinet P, Guillon D. Chem. Mater. 2009; 21: 3282