Annulations with Butenolides and Phthalides: New Entries to Isocoumarins, 3,4-Dihydroisocoumarins, and Benzofurans

Abstract

The reactions of the anions of butenolides and substituted phthalides with sorbate esters and mono-epoxy sorbate esters furnish isocoumarins, 3,4-dihydroisocoumarins, and benzofurans. The yields range from 41% to 71%.

Key words

butenolides - phthalides - sorbate esters - epoxy sorbates - polycyclic ring - isocoumarins - benzofurans - cyclic annulation

• References

• 1 Chen M, Shao CL, Wang KL, Xu Y, She ZG, Wang CY. Tetrahedron 2014; 70: 9132
• 2 Devienne KF, Raddi MS. G, Coelho RG, Vilegas W. Phytomedicine 2005; 12: 378
• 3 Parisot D, Devys M, Férézou JP, Barbier M. Phytochemistry 1983; 22: 1301
• 4 Kraus GA, Dong P. Nat. Prod. Commun. 2015; 10: 1025
• 5 Suresh A, Baiju TV, Kumar T, Namboothiri IN. N. J. Org. Chem. 2019; 84: 3158
• 6 Holmbo SD, Pronin SV. J. Am. Chem. Soc. 2018; 140: 5065
• 7 Ahn S, Han YT. Tetrahedron Lett. 2017; 58: 4779
• 8 Sivasankara C, Satham L, Namboothiri IN. N. J. Org. Chem. 2017; 82: 12939
• 9 Kumar T, Mane V, Namboothiri IN. N. Org. Lett. 2017; 19: 4283
• 10 Kim T, Jeong KH, Kang KS, Nakata M, Ham J. Eur. J. Org. Chem. 2017; 1704
• 11 Kumar T, Satam N, Namboothiri IN. N. Eur. J. Org. Chem. 2016; 3316
• 12 Huang J.-K, Yang Lauderdale T.-L, Shia K.-S. Org. Lett. 2015; 17: 4248
• 13 Hassan NP. S, Naysmith BJ, Sperry J, Brimble MA. Tetrahedron 2015; 71: 7137
• 14 Hugelshofer CL, Magauer T. Angew. Chem. Int. Ed. 2014; 53: 11351
• 15 Brimble MA, Hassan NP. S, Naysmith BJ, Sperry J. J. Org. Chem. 2014; 79: 7169
• 16 Naysmith BJ, Furkert D, Brimble MA. Tetrahedron 2014; 70: 1199
• 17 Schünemann K, Furkert DP, Choi EC, Connelly S, Fraser JD, Sperry J, Brimble MA. Org. Biomol. Chem. 2014; 12: 905
• 18 Naysmith BJ, Brimble MA. Org. Lett. 2013; 15: 2006
• 19 Sperry J, Gibson JS, Sejberg JJ. P, Brimble MA. Org. Biomol. Chem. 2008; 6: 4261
• 20 Brimble MA, Gibson JS, Sejberg JJ. P, Sperry J. Synlett 2008; 6: 867
• 21 Andrey O, Sperry J, Larsen US, Brimble MA. Tetrahedron 2008; 64: 3912
• 22 Gibson JS, Andrey O, Brimble MA. Synthesis 2007; 17: 2611
• 23 Sakulsombat M, Angelin M, Ramström O. Tetrahedron Lett. 2010; 51: 75
• 24 Mal D, Patra A, Roy H. Tetrahedron Lett. 2004; 45: 7895
• 25 Ray S, Patra A, Mal D. Tetrahedron 2008; 64: 3253
• 26 Chakraborty S, Das G, Ghosh S, Mal D. Org. Biomol. Chem. 2016; 14: 10636
• 27 Wang S, Kraus GA. J. Org. Chem. 2018; 83: 15549
• 28 Hayakawa Y, Kobayashi T, Izawa M. J. Antibiot. 2013; 66: 731
• 29 Farina F, Parellada MD. J. Org. Chem. 1988; 53: 3330
• 30 Wang S, Kraus GA. Synlett 2019; 30: 353
• 31 Higuchi Y, Atobe S, Tanaka M, Kamiya I, Yamamoto T, Nomoto A, Sonoda M, Ogawa A. Organometallics 2011; 30: 4539
• 32 Bourguignon JJ, Wermuth CG. J. Org. Chem. 1981; 46: 4889
• 33 Pošta M, Soós V, Beier P. Tetrahedron 2016; 72: 3809
• 34 Clive DL. J, Minaruzzaman, Ou L. J. Org. Chem. 2005; 70: 3318
• 35 Nakayama A, Sato H, Karanjit S, Hayashi N, Oda M, Namba K. Eur. J. Org. Chem. 2018; 4013
• 36 Wang K.-L, Wu Z.-H, Wang Y, Wang C.-Y, Xu Y. Mar. Drugs 2017; 15: 266
• 37a Kawai M, Onaka M, Izumi Y. Bull. Chem. Soc. Jpn. 1988; 61: 2157
• 37b Pettig D, Schoellkopf U. Synthesis 1988; 173
• 38 Yamamoto Y, Suzuki H, Yasuda Y, Iida A, Tomioka K. Tetrahedron Lett. 2008; 49: 4582
• 39 Poldy J, Peakall R, Barrow RA. Eur. J. Org. Chem. 2012; 5818
• 40 He J, Ling J, Chiu P. Chem. Rev. 2014; 114: 8037
• 41 Tang S, Xie X, Huo X, Liang Q, She X, Pan X. Tetrahedron Lett. 2006; 47: 205
• 42 Moore HW, Czerniak R. Med. Res. Rev. 1981; 1: 249
• 43 Tasgin DI, Unaleroglu C. Synthesis 2013; 45: 193
• 44 Wang S, Kraus GA. J. Org. Chem. 2019; 84: 16329
• 45 Freskos JN, Morrow GW, Swenton JS. J. Org. Chem. 1985; 50: 805
• 46 We briefly explored making the natural product. We generated 3-allyl-5-phenylthiobutenolide and reacted it with the epoxy sorbate. The proton NMR of the unpurified products showed that the reaction produced a set of products (with similar R_f values). The double bond of the allyl unit had largely disappeared (probably isomerized at some point during the reaction).