Total Synthesis of Asparenydiol by Two Sonogashira Cross-Coupling Reactions Promoted by Supported Pd and Cu Catalysts

In loving memory of Prof. Adriano Carpita

Abstract

Asparenydiol, which is an important natural compound with potential pharmacological activities, was synthesized through two Sonogashira­ cross-coupling reactions catalyzed by supported Pd and Cu catalysts and by a Mitsunobu etherification. The optimization of the Sonogashira­ couplings allowed the use of catalysts supported on different matrices with good results in terms of catalytic efficiency and yields.

Key words

Asparenydiol - Sonogashira cross-coupling - Mitsunobu etherification - total synthesis - solid-supported palladium catalyst

• References

• 1 Terada K, Honda C, Suwa K, Takeyama S, Oku H, Kamisako W. Chem. Pharm. Bull. (Tokyo) 2011; 43: 564
• 2 Zhang HJ, Sydara K, Tan GT, Ma C, Southavong B, Soejarto DD, Pezzuto JM, Fong HH. S. J. Nat. Prod. 2004; 67: 194
• 3 Jayashree GV, Kumar KH, Krupashree K, Rachitha P, Khanum F. Ind. Crops Prod. 2015; 78: 102
• 4 Dembitsky VM. Lipids 2006; 41: 883
• 5 Fletcher S. Org. Chem. Front. 2015; 2: 739
• 6 Swamy KC. K, Kumar NN. B, Balaraman E, Kumar KV. P. P. Chem. Rev. 2009; 109: 2551
• 7 Doucet H, Hierso JC. Angew. Chem. Int. Ed. 2007; 46: 834
• 8 Chinchilla R, Nájera C. Chem. Rev. 2007; 107: 874
• 9 Plenio H. Angew. Chem. Int. Ed. 2008; 47: 6954
• 10 Krascsenicsová K, Kasák P, Putala M, Walla P, Uray G, Kappe CO. Chem. Commun. 2004; 10: 2606
• 11 Fusini G, Barsanti D, Angelici G, Casotti G, Canale A, Benelli G, Lucchi A, Carpita A. Tetrahedron 2018; 74: 4381
• 12 Yin L, Liebscher J. Chem. Rev. 2007; 107: 133
• 13 Garrais S, Turkington J, Goldring WP. D. Tetrahedron 2009; 65: 8418
• 14 Carpita A, Mannocci L, Rossi R. Eur. J. Org. Chem. 2005; 1859
• 15 Newton S, Carter CF, Pearson CM, De C Alves L, Lange H, Thansandote P, Ley SV. Angew. Chem. Int. Ed. 2014; 53: 4915
• 16 Sabitha G, Das SK, Ankireddy P, Yadav JS. Tetrahedron Lett. 2013; 54: 1097
• 17 Vaz B, Pereira R, Pérez M, Álvarez R, De Lera AR. J. Org. Chem. 2008; 73: 6534
• 18 Hulot C, Blond G, Suffert J. J. Am. Chem. Soc. 2008; 130: 5046
• 19 Hashmi AS. K, Graf K, Ackermann M, Rominger F. ChemCatChem 2013; 5: 1200
• 20 Takeuchi R, Tanabe K, Tanaka S. J. Org. Chem. 2000; 65: 1558
• 21 Nishimura T, Araki H, Maeda Y, Uemura S. Org. Lett. 2003; 5: 2997
• 22 Bates CG, Saejueng P, Venkataraman D. Org. Lett. 2004; 6: 1441
• 23 Ranu BC, Chattopadhyay K. Org. Lett. 2007; 9: 2409
• 24 Ranu BC, Adak L, Chattopadhyay K. J. Org. Chem. 2008; 73: 5609
• 25 Ogawa T, Ohta K, Iijima T, Suzuki T, Ohta S, Endo Y. Bioorg. Med. Chem. 2009; 17: 1109
• 26 Evangelisti C, Balerna A, Psaro R, Fusini G, Carpita A, Benfatto M. ChemPhysChem 2017; 18: 1921
• 27 Balerna A, Evangelisti C, Tiozzo C. X-ray Spectrom. 2017; 46: 82
• 28 Evangelisti C, Panziera N, Pertici P, Vitulli G, Salvadori P, Battocchio C, Polzonetti G. J. Catal. 2009; 262: 287
• 29 Jumde RP, Marelli M, Scotti N, Mandoli A, Psaro R, Evangelisti C. J. Mol. Catal. A: Chem. 2016; 414: 55
• 30 Laudadio G, Fusini G, Casotti G, Evangelisti C, Angelici G, Carpita A. J. Flow Chem. 2019; 9: 133
• 31 Biffis A, Centomo P, Del Zotto A, Zecca M. Chem. Rev. 2018; 118: 2249
• 32 Weir JR, Patel BA, Heck RF. J. Org. Chem. 1980; 45: 4926
• 33 Sauerberg P, Bury PS, Mogensen JP, Deussen HJ, Pettersson I, Fleckner J, Nehlin J, Frederiksen KS, Albrektsen T, Din N, Svensson LA, Ynddal L, Wulff EM, Jeppesen L. J. Med. Chem. 2003; 46: 4883
• 34 Bellina F, Carpita A, Corradi C, Rossi R. Synth. Commun. 1996; 26: 3297
• 35 Li L, Shen X, Xu QH, Yao SQ. Angew. Chem. Int. Ed. 2013; 52: 424
• 36 López-Pelegrín JA, Wentworth P, Sieber F, Metz WA, Janda KD. J. Org. Chem. 2000; 65: 8527
• 37 Sauerberg P, Mogensen JP, Jeppesen L, Bury PS, Fleckner J, Olsen GS, Jeppesen CB, Wulff EM, Pihera P, Havranek M, Polivka Z, Pettersson I. Bioorg. Med. Chem. Lett. 2007; 17: 3198
• 38 Kiuchi H, Takahashi D, Funaki K, Sato T, Oi S. Org. Lett. 2012; 14: 4502
• 39 Rossi R, Carpita A, Lippolis V, Benetti M. Gazz. Chim. Ital. 1990; 120: 783