Total Synthesis of (R)-Argentilactone and (R)-Goniothalamin Using a Free-Radical Photoredox Approach to α,β-Unsaturated δ-Lactones

To the memory of our colleagues Rocío Patiño, Barbarín Arreguín and Gaudencio Anastacio.

Abstract

α,β-Unsaturated δ-lactones are structural motifs found in diverse pharmacologically active natural products. In fact, the unsaturated lactone is often responsible for the biological activity. Herein, we report a new approach for the syntheses of (R)-argentilactone and (R)-goniothalamin based on a photoredox intermolecular iodolactonization mediated by a photoredox process. This new approach, already employed in our research group, stands as a new methodology to achieve several natural products containing α,β-unsaturated δ-lactones.

Key words

free-radical lactonization - photoredox catalysis - argentilactone - goniothalamin - unsaturated lactones

Publication History

Received: 18 June 2021

Accepted after revision: 14 July 2021

Accepted Manuscript online:
14 July 2021

Article published online:
11 August 2021

• References

• 1 Priestap HA, Bonafede JD, Rúveda EA. Phytochemistry 1977; 16: 1579
• 2 Hlubucek JR, Robertson AV. Aust. J. Chem. 1967; 20: 2199
• 3 Waechter AI, Ferreira ME, Fournet A, de Arias AR, Nakayama H, Torres S, Hocquemiller R, Cavé A. Planta Med. 1997; 63: 433
• 4 Matsuda M, Endo Y, Fushiya S, Endo T, Nozoe S. Hetero­cycles 1994; 38: 1229
• 5 Ali AM, Mackeen MM, Hamid M, Aun QB, Zauyah H, Azimahtol HL. P, Kawazu K. Planta Med. 1997; 63: 81
• 6 Hawariah W, Stanslas J. In Vivo 1998; 12: 403
• 7 Pilli RA, De Toledo I, Meirelles MA, Grigolo TA. Curr. Med. Chem. 2019; 26: 7372
• 8 Weber A, Döhl K, Sachs J, Nordschild AC. M, Schröder D, Kulik A, Fischer T, Schmitt L, Teusch N, Pietruszka J. Bioorg. Med. Chem. 2017; 25: 6115
• 9 de Fátima Â, Kohn LK, de Carvalho JE, Pilli RA. Bioorg. Med. Chem. 2006; 14: 622
• 10a Boger DL, Hikota M, Lewis BM. J. Org. Chem. 1997; 62: 1748
• 10b Saeed M, Abbas M, Khan KM, Voelter W. Z. Naturforsch., B 2001; 56: 325
• 10c Saeed M, Ilg T, Schick M, Abbas M, Voelter W. Tetrahedron Lett. 2001; 42: 7401
• 10d Hansen TV. Tetrahedron: Asymmetry 2002; 13: 547
• 10e de Fatima Â, Kohn LK, Antônio MA, de Carvalho JE, Pilli RA. Bioorg. Med. Chem. 2004; 12: 5437
• 10f Sabitha G, Fatima N, Yadav SJ. S. Synthesis 2006; 2879
• 11a O’Connor B, Just G. Tetrahedron Lett. 1986; 27: 5201
• 11b Job A, Wolberg M, Müller M, Enders D. Synlett 2001; 1796
• 11c de Fátima Â, Pilli RA. ARKIVOC 2003; (x): 118
• 11d de Fátima Â, Pilli RA. Tetrahedron Lett. 2003; 44: 8721
• 12a Peng XS, Li AP, Wu TW, Pan XF. Chin. Chem. Lett. 2002; 13: 519
• 12b Peng X, Li A, Shen H, Wu T, Pan X. J. Chem. Res. 2002; 330
• 12c Fournier L, Kocienski P, Pons J.-M. Tetrahedron 2004; 60: 1659
• 12d de Fátima Â, Kohn LK, Antônio MA, de Carvalho JE, Pilli RA. Bioorg. Med. Chem. 2005; 13: 2927
• 12e Poppisil J, Markó IE. Tetrahedron Lett. 2006; 47: 5933
• 12f Bressy C, Bargiggia F, Guyonnet M, Arseniyadis S, Cossy J. Synlett 2009; 565
• 12g Das B, Nagendra S, Reddy CR. Tetrahedron: Asymmetry 2011; 22: 1249
• 12h Yadav JS, Bhunia DC, Ganganna B, Singh VK. RSC Adv. 2013; 3: 5254
• 12i Ramesh P, Raju A, Fadnavis NW. Tetrahedron: Asymmetry 2015; 26: 1251
• 12j Meruva SB, Rao RK, Mohammed A, Dahanukar VH, Kumar UK. S, Dubey PK. Synth. Commun. 2016; 46: 187
• 12k Ramesh P, Rao TP. J. Nat. Prod. 2016; 79: 2060
• 12l Pastre JC, Murray PR. D, Browne DL, Brancaglion GA, Galaverna RS, Pilli RA, Ley SV. ACS Omega 2020; 5: 18472
• 13 Hunter TJ, O’Doherty GA. Org. Lett. 2001; 3: 2777
• 14 Buck SB, Hardouin C, Ichikawa S, Soenen DR, Gauss C.-M, Hwang I, Swingle MR, Bonness KM, Honkanen RE, Boger DL. J. Am. Chem. Soc. 2003; 125: 15694
• 15 Fan Q, Lin L, Huang Y, Feng X, Zhang G. Org. Lett. 2004; 6: 2185
• 16 Fan Q, Lin L, Huang Y, Feng X. Eur. J. Org. Chem. 2005; 3542
• 17 Bazan-Tejeda B, Georgy M, Campagne J.-M. Synlett 2004; 720
• 18 Moreau X, Bazan-Tejeda B, Campagne J.-M. J. Am. Chem. Soc. 2005; 127: 7288
• 19 Keck GE, Knutson CE, Wiles SA. Org. Lett. 2001; 3: 707
• 20 Boucard V, Broustal G, Campagne J.-M. Eur. J. Org. Chem. 2007; 225
• 21 Avula SK, Das B, Csuk R, Al-Rawahi A, Al-Harrasi A. Molecules 2020; 25: 1905
• 22 León-Rayo DF, Morales-Chamorro M, Cordero-Vargas A. Eur. J. Org. Chem. 2016; 1739
• 23 Mateus-Ruiz JB, Cordero-Vargas A. J. Org. Chem. 2019; 84: 11848
• 24 Crimmins MT, Ellis JM, Emmitte KA, Haile PA, McDougall PJ, Parrish JD, Zuccarello L. Chem. Eur. J. 2009; 15: 9223
• 25 Povie G, Ford L, Pozzi D, Soulard V, Villa G, Renaud P. Angew. Chem. Int. Ed. 2016; 55: 11221
• 26 Liu Z.-Y, Ji J.-X, Li B.-G. J. Chem. Res. 2004; 61
• 27 Coutrot P, Grison C, Bômont C. J. Organomet. Chem. 1999; 586: 208
• 28 Hendrix MA. J, Jennings MP. Tetrahedron Lett. 2010; 51: 4260
• 29 Fukuzaki T, Kobayashi S, Hibi T, Ikuma Y, Ishihara J, Kanoh N, Murai A. Org. Lett. 2002; 4: 2877
• 30 Pandey R, Prakash R. Can. J. Chem. 2018; 96: 1061
• 31 Pospíšil J. Tetrahedron Lett. 2011; 52: 2348
• 32 Beck G, Kesseler K, Baader E, Bartmann W, Bergmann A, Granzer E, Jendralla H, Kerekjarto BV, Krause R, Paulus E, Schubert W, Wess G. J. Med. Chem. 1990; 33: 52
• 33 Tate EW, Dixon DJ, Ley SV. Org. Biomol. Chem. 2006; 4: 1698
• 34 Štambaský J, Kapras V, Štefko M, Kysilka O, Hocek M, Malkov AV, Kočovský P. J. Org. Chem. 2011; 76: 7781
• 35 Prasad K, Swain B. J. Org. Chem. 2011; 76: 2029
• 36 Taylor RJ. K, Wiggins K, Robinson DH. Synthesis 1990; 589
• 37a Mase N, Inoue A, Nishio M, Takabe K. Bioorg. Med. Chem. Lett. 2009; 19: 3955
• 37b Blaser F, Deschenaux P.-F, Kallimopoulos T, Jacot-Guillarmod A. Helv. Chim. Acta 1991; 74: 141
• 38 Coutrot P, Grison C, Bômont C. Tetrahedron Lett. 1994; 35: 8381
• 39 Raghavan S, Rajendar S. Tetrahedron Lett. 2015; 56: 4371